# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_hyvl108_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2504497'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;Department of Chemistry, University of California, San Diego
United States of America
;
_audit_update_record             
;
2025-11-20 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-06-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Bi F3 N'
_chemical_formula_sum            'C21 H17 Bi F3 N'
_chemical_formula_weight         549.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5151(13)
_cell_length_b                   9.3054(10)
_cell_length_c                   16.450(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.005(3)
_cell_angle_gamma                90
_cell_volume                     1761.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3163
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.197
_shelx_estimated_absorpt_T_min   0.147
_exptl_absorpt_coefficient_mu    10.042
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1052 before and 0.0751 after correction.
The Ratio of minimum to maximum transmission is 0.5836.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.071
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18306
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         1.770
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3898
_reflns_number_total             4392
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 v2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT v8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         1.115
_refine_diff_density_min         -1.291
_refine_diff_density_rms         0.217
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+4.0902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0851
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C6(H6), C4(H4), C11(H11), C17(H17),
 C5(H5), C12(H12), C3(H3), C14(H14), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.72135(2) 0.48399(2) 0.51183(2) 0.01220(7) Uani 1 1 d . . . . .
F3 F 0.8406(3) 0.1850(4) 0.5190(2) 0.0322(8) Uani 1 1 d . . . . .
F2 F 0.7788(3) 0.2255(4) 0.6396(2) 0.0324(8) Uani 1 1 d . . . . .
F1 F 0.6585(3) 0.1567(3) 0.5440(2) 0.0327(8) Uani 1 1 d . . . . .
C15 C 0.8729(3) 0.5570(5) 0.5919(3) 0.0129(8) Uani 1 1 d . . . . .
C18 C 0.9052(4) 0.9123(6) 0.3833(3) 0.0225(11) Uani 1 1 d . . . . .
H18 H 0.986563 0.925872 0.379012 0.027 Uiso 1 1 calc R U . . .
N1 N 0.7016(3) 0.7705(4) 0.5350(3) 0.0149(8) Uani 1 1 d . . . . .
C19 C 0.8316(4) 0.9480(6) 0.3178(3) 0.0206(10) Uani 1 1 d . . . . .
H19 H 0.861555 0.984500 0.268865 0.025 Uiso 1 1 calc R U . . .
C1 C 0.7496(4) 0.2430(6) 0.5593(3) 0.0222(11) Uani 1 1 d . . . . .
C20 C 0.7140(4) 0.9290(6) 0.3257(3) 0.0221(11) Uani 1 1 d . . . . .
H20 H 0.662314 0.953163 0.281562 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5354(4) 0.6657(5) 0.6052(3) 0.0160(9) Uani 1 1 d . . . . .
C9 C 0.7718(4) 0.7974(5) 0.6109(3) 0.0165(10) Uani 1 1 d . . . . .
H9A H 0.720936 0.788417 0.657941 0.020 Uiso 1 1 calc R U . . .
H9B H 0.801283 0.897362 0.610048 0.020 Uiso 1 1 calc R U . . .
C21 C 0.6693(4) 0.8753(5) 0.3970(3) 0.0198(10) Uani 1 1 d . . . . .
H21 H 0.587696 0.864625 0.401289 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4455(4) 0.6967(6) 0.6577(3) 0.0189(10) Uani 1 1 d . . . . .
H6 H 0.415268 0.791598 0.659900 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5764(4) 0.7803(5) 0.5482(3) 0.0183(10) Uani 1 1 d . . . . .
H8A H 0.533381 0.771129 0.495267 0.022 Uiso 1 1 calc R U . . .
H8B H 0.558657 0.876045 0.570932 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4424(4) 0.4519(6) 0.7027(3) 0.0199(10) Uani 1 1 d . . . . .
H4 H 0.410193 0.378458 0.735152 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7437(4) 0.8370(5) 0.4625(3) 0.0141(9) Uani 1 1 d . . . . .
C11 C 0.9704(4) 0.7443(6) 0.6695(3) 0.0193(10) Uani 1 1 d . . . . .
H11 H 0.971193 0.839592 0.690307 0.023 Uiso 1 1 calc R U . . .
C17 C 0.8632(4) 0.8578(6) 0.4541(3) 0.0200(10) Uani 1 1 d . . . . .
H17 H 0.915752 0.834008 0.497881 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8744(4) 0.6955(5) 0.6231(3) 0.0151(9) Uani 1 1 d . . . . .
C5 C 0.3998(4) 0.5898(6) 0.7066(3) 0.0207(10) Uani 1 1 d . . . . .
H5 H 0.339522 0.612040 0.742540 0.025 Uiso 1 1 calc R U . . .
C2 C 0.5806(4) 0.5252(5) 0.6023(3) 0.0147(9) Uani 1 1 d . . . . .
C12 C 1.0649(4) 0.6540(6) 0.6854(3) 0.0242(11) Uani 1 1 d . . . . .
H12 H 1.129674 0.687223 0.717425 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5329(4) 0.4194(6) 0.6513(3) 0.0173(10) Uani 1 1 d . . . . .
H3 H 0.562301 0.324101 0.649632 0.021 Uiso 1 1 calc R U . . .
C14 C 0.9688(4) 0.4666(6) 0.6071(3) 0.0188(10) Uani 1 1 d . . . . .
H14 H 0.969001 0.372068 0.585357 0.023 Uiso 1 1 calc R U . . .
C13 C 1.0642(4) 0.5158(6) 0.6544(4) 0.0214(11) Uani 1 1 d . . . . .
H13 H 1.128657 0.454068 0.665274 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C15 2.255(4) . ?
Bi1 N1 2.704(4) . ?
Bi1 C1 2.393(5) . ?
Bi1 C2 2.271(5) . ?
F3 C1 1.369(6) . ?
F2 C1 1.362(6) . ?
F1 C1 1.338(6) . ?
C15 C10 1.388(7) . ?
C15 C14 1.403(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(7) . ?
C18 C17 1.375(7) . ?
N1 C9 1.486(6) . ?
N1 C8 1.468(6) . ?
N1 C16 1.442(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(7) . ?
C7 C6 1.401(7) . ?
C7 C8 1.508(7) . ?
C7 C2 1.408(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.522(6) . ?
C21 H21 0.9500 . ?
C21 C16 1.400(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.395(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.376(8) . ?
C4 C3 1.398(7) . ?
C16 C17 1.401(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.396(6) . ?
C11 C12 1.393(7) . ?
C17 H17 0.9500 . ?
C5 H5 0.9500 . ?
C2 C3 1.398(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(8) . ?
C3 H3 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.401(7) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 Bi1 N1 71.82(15) . . ?
C15 Bi1 C1 89.88(17) . . ?
C15 Bi1 C2 97.00(16) . . ?
C1 Bi1 N1 152.77(15) . . ?
C2 Bi1 N1 71.06(15) . . ?
C2 Bi1 C1 92.10(18) . . ?
C10 C15 Bi1 119.7(3) . . ?
C10 C15 C14 119.4(4) . . ?
C14 C15 Bi1 120.8(4) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.5(5) . . ?
C9 N1 Bi1 103.8(3) . . ?
C8 N1 Bi1 99.8(3) . . ?
C8 N1 C9 112.0(4) . . ?
C16 N1 Bi1 105.9(3) . . ?
C16 N1 C9 115.7(4) . . ?
C16 N1 C8 117.1(4) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.2(5) . . ?
C20 C19 H19 120.9 . . ?
F3 C1 Bi1 108.0(3) . . ?
F2 C1 Bi1 117.1(3) . . ?
F2 C1 F3 104.8(4) . . ?
F1 C1 Bi1 113.8(3) . . ?
F1 C1 F3 106.3(4) . . ?
F1 C1 F2 106.0(5) . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C6 C7 C8 119.5(5) . . ?
C6 C7 C2 119.7(5) . . ?
C2 C7 C8 120.7(4) . . ?
N1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
N1 C9 C10 113.8(4) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C16 120.4(4) . . ?
C16 C21 H21 119.8 . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.7(5) . . ?
C5 C6 H6 119.7 . . ?
N1 C8 C7 112.2(4) . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.3(5) . . ?
C3 C4 H4 119.9 . . ?
C21 C16 N1 122.1(4) . . ?
C21 C16 C17 117.7(5) . . ?
C17 C16 N1 120.1(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.3(5) . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C15 C10 C9 122.0(4) . . ?
C15 C10 C11 120.2(4) . . ?
C11 C10 C9 117.7(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5 120.1 . . ?
C7 C2 Bi1 116.9(3) . . ?
C3 C2 Bi1 124.3(4) . . ?
C3 C2 C7 118.7(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.1 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 H3 119.6 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 H14 120.0 . . ?
C12 C13 C14 120.1(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C15 C10 C9 5.2(6) . . . . ?
Bi1 C15 C10 C11 -176.8(3) . . . . ?
Bi1 C15 C14 C13 177.5(4) . . . . ?
Bi1 N1 C9 C10 31.2(4) . . . . ?
Bi1 N1 C8 C7 45.0(4) . . . . ?
Bi1 N1 C16 C21 93.5(5) . . . . ?
Bi1 N1 C16 C17 -82.9(5) . . . . ?
Bi1 C2 C3 C4 -176.9(3) . . . . ?
C15 C14 C13 C12 -0.8(8) . . . . ?
C18 C19 C20 C21 -0.2(8) . . . . ?
N1 C9 C10 C15 -28.7(6) . . . . ?
N1 C9 C10 C11 153.3(4) . . . . ?
N1 C16 C17 C18 175.7(5) . . . . ?
C19 C18 C17 C16 -0.2(8) . . . . ?
C19 C20 C21 C16 -1.0(8) . . . . ?
C20 C21 C16 N1 -175.0(5) . . . . ?
C20 C21 C16 C17 1.5(7) . . . . ?
C7 C6 C5 C4 -0.8(7) . . . . ?
C7 C2 C3 C4 -0.4(7) . . . . ?
C9 N1 C8 C7 -64.3(5) . . . . ?
C9 N1 C16 C21 -152.1(4) . . . . ?
C9 N1 C16 C17 31.4(6) . . . . ?
C21 C16 C17 C18 -0.9(7) . . . . ?
C6 C7 C8 N1 146.0(4) . . . . ?
C6 C7 C2 Bi1 177.7(3) . . . . ?
C6 C7 C2 C3 1.0(6) . . . . ?
C8 N1 C9 C10 137.9(4) . . . . ?
C8 N1 C16 C21 -16.7(7) . . . . ?
C8 N1 C16 C17 166.9(4) . . . . ?
C8 C7 C6 C5 175.1(4) . . . . ?
C8 C7 C2 Bi1 2.3(5) . . . . ?
C8 C7 C2 C3 -174.5(4) . . . . ?
C16 N1 C9 C10 -84.4(5) . . . . ?
C16 N1 C8 C7 158.6(4) . . . . ?
C11 C12 C13 C14 0.0(8) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C10 C15 C14 C13 0.9(7) . . . . ?
C10 C11 C12 C13 0.6(8) . . . . ?
C5 C4 C3 C2 -0.8(7) . . . . ?
C2 C7 C6 C5 -0.4(7) . . . . ?
C2 C7 C8 N1 -38.5(6) . . . . ?
C12 C11 C10 C15 -0.5(7) . . . . ?
C12 C11 C10 C9 177.5(5) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C14 C15 C10 C9 -178.2(4) . . . . ?
C14 C15 C10 C11 -0.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl107_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2504513'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;Department of Chemistry, University of California, San Diego
United States of America
;
_audit_update_record             
;
2025-11-20 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Bi F6 N O S'
_chemical_formula_sum            'C14 H8 Bi F6 N O S'
_chemical_formula_weight         561.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5658(6)
_cell_length_b                   9.3066(6)
_cell_length_c                   19.3565(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.575(3)
_cell_angle_gamma                90
_cell_volume                     1540.07(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2343
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      3.24
_shelx_estimated_absorpt_T_max   0.145
_shelx_estimated_absorpt_T_min   0.123
_exptl_absorpt_coefficient_mu    11.651
_exptl_absorpt_correction_T_max  0.4912
_exptl_absorpt_correction_T_min  0.3022
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1058 before and 0.0362 after correction.
The Ratio of minimum to maximum transmission is 0.6152.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11393
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         3.236
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3075
_reflns_number_total             3337
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0166
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0095P)²+1.6015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0342
_refine_ls_wR_factor_ref         0.0350
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: F4(0.4) F5(0.4) F6'(0.6) F6(0.4) F5'(0.6) F4'(0.6)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C5(H5), C12(H12), C13(H13), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.57501(2) 0.70498(2) 0.57919(2) 0.01583(4) Uani 1 1 d . . . . .
S1 S 0.17467(8) 0.71814(7) 0.56310(3) 0.01484(14) Uani 1 1 d . . . . .
O1 O 0.0064(2) 0.7211(2) 0.56202(10) 0.0207(4) Uani 1 1 d . . . . .
F3 F 0.8169(2) 0.7283(2) 0.70510(9) 0.0298(4) Uani 1 1 d . . . . .
F2 F 0.6330(2) 0.5867(2) 0.73318(8) 0.0312(4) Uani 1 1 d . . . . .
C7 C 0.4153(3) 0.8331(3) 0.64491(14) 0.0151(6) Uani 1 1 d . . . . .
F1 F 0.8048(2) 0.5116(2) 0.66503(9) 0.0312(4) Uani 1 1 d . . . . .
C4 C 0.2129(3) 0.9862(3) 0.72606(14) 0.0190(6) Uani 1 1 d . . . . .
H4 H 0.145375 1.039340 0.753649 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4748(3) 0.9195(3) 0.69871(14) 0.0162(6) Uani 1 1 d . . . . .
H6 H 0.584629 0.926358 0.708365 0.019 Uiso 1 1 calc R U . . .
C3 C 0.1498(3) 0.8988(3) 0.67334(13) 0.0161(6) Uani 1 1 d . . . . .
H3 H 0.039818 0.889944 0.664703 0.019 Uiso 1 1 calc R U . . .
C2 C 0.2528(3) 0.8245(3) 0.63359(13) 0.0141(6) Uani 1 1 d . . . . .
N1 N 0.2610(3) 0.7554(3) 0.49729(11) 0.0173(5) Uani 1 1 d . . . . .
C5 C 0.3731(4) 0.9967(3) 0.73879(14) 0.0189(6) Uani 1 1 d . . . . .
H5 H 0.414680 1.056843 0.775085 0.023 Uiso 1 1 calc R U . . .
C1 C 0.2455(4) 0.8915(3) 0.46839(15) 0.0216(6) Uani 1 1 d . . . . .
C12 C 0.1905(4) 0.2961(3) 0.60033(16) 0.0265(7) Uani 1 1 d . . . . .
H12 H 0.117910 0.219702 0.603994 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2473(4) 0.5427(3) 0.58013(13) 0.0171(6) Uani 1 1 d . . . . .
C13 C 0.1373(4) 0.4346(3) 0.58563(14) 0.0213(6) Uani 1 1 d . . . . .
H13 H 0.028528 0.454677 0.579514 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4084(3) 0.5196(3) 0.58887(13) 0.0178(6) Uani 1 1 d . . . . .
C11 C 0.3491(4) 0.2697(3) 0.60960(15) 0.0268(7) Uani 1 1 d . . . . .
H11 H 0.384708 0.175033 0.620029 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7154(3) 0.6275(4) 0.67910(15) 0.0223(6) Uani 1 1 d . . . . .
C10 C 0.4583(4) 0.3804(3) 0.60387(14) 0.0217(6) Uani 1 1 d . . . . .
H10 H 0.566975 0.360206 0.610272 0.026 Uiso 1 1 calc R U . . .
F4 F 0.2154(12) 0.8857(7) 0.4026(3) 0.0496(18) Uani 0.4 1 d . . P A 2
F5 F 0.3870(7) 0.9522(7) 0.4771(5) 0.062(2) Uani 0.4 1 d . . P A 2
F6' F 0.1133(6) 0.9056(6) 0.4265(3) 0.0735(19) Uani 0.6 1 d . . P A 1
F6 F 0.1480(11) 0.9746(8) 0.4941(5) 0.060(3) Uani 0.4 1 d . . P A 2
F5' F 0.2383(7) 1.0053(5) 0.5095(3) 0.0497(16) Uani 0.6 1 d . . P A 1
F4' F 0.3563(7) 0.9223(5) 0.4259(3) 0.0581(15) Uani 0.6 1 d . . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C7 2.265(3) . ?
Bi1 C9 2.254(3) . ?
Bi1 C8 2.327(3) . ?
S1 O1 1.440(2) . ?
S1 C2 1.782(3) . ?
S1 N1 1.552(2) . ?
S1 C14 1.771(3) . ?
F3 C8 1.355(4) . ?
F2 C8 1.352(3) . ?
C7 C6 1.387(4) . ?
C7 C2 1.397(4) . ?
F1 C8 1.359(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.388(4) . ?
C4 C5 1.383(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.400(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.390(4) . ?
N1 C1 1.388(4) . ?
C5 H5 0.9500 . ?
C1 F4 1.285(6) . ?
C1 F5 1.338(6) . ?
C1 F6' 1.357(5) . ?
C1 F6 1.263(8) . ?
C1 F5' 1.328(6) . ?
C1 F4' 1.325(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(4) . ?
C12 C11 1.381(5) . ?
C14 C13 1.387(4) . ?
C14 C9 1.396(4) . ?
C13 H13 0.9500 . ?
C9 C10 1.389(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.400(5) . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 Bi1 C8 89.74(10) . . ?
C9 Bi1 C7 87.05(10) . . ?
C9 Bi1 C8 89.47(10) . . ?
O1 S1 C2 109.17(13) . . ?
O1 S1 N1 120.78(13) . . ?
O1 S1 C14 111.10(13) . . ?
N1 S1 C2 109.17(13) . . ?
N1 S1 C14 100.32(13) . . ?
C14 S1 C2 105.00(13) . . ?
C6 C7 Bi1 121.4(2) . . ?
C6 C7 C2 117.8(2) . . ?
C2 C7 Bi1 120.83(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C4 C3 H3 121.1 . . ?
C4 C3 C2 117.8(3) . . ?
C2 C3 H3 121.1 . . ?
C7 C2 S1 118.3(2) . . ?
C3 C2 S1 118.6(2) . . ?
C3 C2 C7 123.0(2) . . ?
C1 N1 S1 119.8(2) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
F4 C1 N1 111.7(4) . . ?
F4 C1 F5 105.5(6) . . ?
F5 C1 N1 105.7(3) . . ?
F6' C1 N1 112.6(3) . . ?
F6 C1 N1 116.6(4) . . ?
F6 C1 F4 108.7(6) . . ?
F6 C1 F5 108.0(6) . . ?
F5' C1 N1 119.5(3) . . ?
F5' C1 F6' 102.3(4) . . ?
F4' C1 N1 113.1(3) . . ?
F4' C1 F6' 102.2(4) . . ?
F4' C1 F5' 105.2(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C14 S1 116.8(2) . . ?
C13 C14 C9 123.4(3) . . ?
C9 C14 S1 119.9(2) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 H13 120.9 . . ?
C14 C9 Bi1 119.8(2) . . ?
C10 C9 Bi1 122.9(2) . . ?
C10 C9 C14 117.3(3) . . ?
C12 C11 H11 119.5 . . ?
C12 C11 C10 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
F3 C8 Bi1 112.35(19) . . ?
F3 C8 F1 105.5(2) . . ?
F2 C8 Bi1 117.54(18) . . ?
F2 C8 F3 105.1(2) . . ?
F2 C8 F1 105.1(2) . . ?
F1 C8 Bi1 110.34(18) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C7 C6 C5 -179.5(2) . . . . ?
Bi1 C7 C2 S1 -3.4(3) . . . . ?
Bi1 C7 C2 C3 178.7(2) . . . . ?
Bi1 C9 C10 C11 179.7(2) . . . . ?
S1 N1 C1 F4 -132.5(5) . . . . ?
S1 N1 C1 F5 113.3(5) . . . . ?
S1 N1 C1 F6' -82.7(5) . . . . ?
S1 N1 C1 F6 -6.6(7) . . . . ?
S1 N1 C1 F5' 37.3(5) . . . . ?
S1 N1 C1 F4' 162.0(4) . . . . ?
S1 C14 C13 C12 -178.8(2) . . . . ?
S1 C14 C9 Bi1 -1.2(3) . . . . ?
S1 C14 C9 C10 178.4(2) . . . . ?
O1 S1 C2 C7 178.5(2) . . . . ?
O1 S1 C2 C3 -3.6(2) . . . . ?
O1 S1 N1 C1 62.2(3) . . . . ?
O1 S1 C14 C13 3.7(2) . . . . ?
O1 S1 C14 C9 -174.8(2) . . . . ?
C7 C6 C5 C4 1.0(4) . . . . ?
C4 C3 C2 S1 -177.2(2) . . . . ?
C4 C3 C2 C7 0.7(4) . . . . ?
C6 C7 C2 S1 178.2(2) . . . . ?
C6 C7 C2 C3 0.3(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C2 S1 N1 C1 -65.5(3) . . . . ?
C2 S1 C14 C13 121.6(2) . . . . ?
C2 S1 C14 C9 -56.9(2) . . . . ?
C2 C7 C6 C5 -1.2(4) . . . . ?
N1 S1 C2 C7 -47.6(2) . . . . ?
N1 S1 C2 C3 130.4(2) . . . . ?
N1 S1 C14 C13 -125.1(2) . . . . ?
N1 S1 C14 C9 56.3(2) . . . . ?
C5 C4 C3 C2 -0.9(4) . . . . ?
C12 C11 C10 C9 0.2(4) . . . . ?
C14 S1 C2 C7 59.3(2) . . . . ?
C14 S1 C2 C3 -122.8(2) . . . . ?
C14 S1 N1 C1 -175.5(2) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C13 C12 C11 C10 -0.5(4) . . . . ?
C13 C14 C9 Bi1 -179.6(2) . . . . ?
C13 C14 C9 C10 -0.1(4) . . . . ?
C9 C14 C13 C12 -0.3(4) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl104_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2504521'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;Department of Chemistry, University of California, San Diego
United States of America
;
_audit_update_record             
;
2025-11-20 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-02-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Bi F3 N O'
_chemical_formula_sum            'C16 H15 Bi F3 N O'
_chemical_formula_weight         503.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3263(7)
_cell_length_b                   9.3742(6)
_cell_length_c                   17.9914(13)
_cell_angle_alpha                89.902(2)
_cell_angle_beta                 77.349(2)
_cell_angle_gamma                88.952(2)
_cell_volume                     1534.48(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2460
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.147
_shelx_estimated_absorpt_T_min   0.115
_exptl_absorpt_coefficient_mu    11.522
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1076 before and 0.0903 after correction.
The Ratio of minimum to maximum transmission is 0.6122.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21237
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.284
_diffrn_reflns_theta_min         2.173
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5979
_reflns_number_total             6816
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'APEX4 v2022.1-1 (Bruker, 2022)'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         1.509
_refine_diff_density_min         -2.045
_refine_diff_density_rms         0.256
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6816
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+2.2503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1004
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(C8)
3.a Secondary CH2 refined with riding coordinates:
 C3'(H3'A,H3'B), C10(H10A,H10B), C10'(H10C,H10D), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C8(H8), C12(H12), C14(H14), C12'(H12'), C15(H15), C5(H5),
 C7'(H7'), C14'(H14'), C13(H13), C6'(H6'), C8'(H8'), C13'(H13'), C5'(H5'),
 C15'(H15')
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2'(H2'A,H2'B,H2'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.48158(2) 0.25524(2) 0.07373(2) 0.01052(8) Uani 1 1 d . . . . .
Bi1' Bi 0.77411(2) 0.62742(2) 0.45698(2) 0.01113(8) Uani 1 1 d . . . . .
F2' F 0.6873(4) 0.9640(4) 0.4688(2) 0.0236(8) Uani 1 1 d . . . . .
O1 O 0.8707(5) 0.1872(5) -0.0242(2) 0.0192(10) Uani 1 1 d . . . . .
F1 F 0.1774(4) 0.1588(4) 0.1667(2) 0.0220(8) Uani 1 1 d . . . . .
N1 N 0.7763(5) 0.2740(5) 0.0331(3) 0.0102(10) Uani 1 1 d . . . . .
F2 F 0.2442(4) 0.3258(4) 0.2323(2) 0.0225(8) Uani 1 1 d . . . . .
F3 F 0.1592(4) 0.3791(4) 0.1338(2) 0.0210(8) Uani 1 1 d . . . . .
F3' F 0.8314(4) 0.9034(4) 0.5428(2) 0.0249(9) Uani 1 1 d . . . . .
N1' N 0.7990(6) 0.4539(5) 0.3354(3) 0.0131(10) Uani 1 1 d . . . . .
O1' O 0.9076(5) 0.3406(5) 0.3157(3) 0.0207(10) Uani 1 1 d . . . . .
F1' F 0.6024(5) 0.8544(4) 0.5741(2) 0.0284(9) Uani 1 1 d . . . . .
C3' C 0.8280(7) 0.5513(7) 0.2705(3) 0.0175(13) Uani 1 1 d . . . . .
H3'A H 0.733717 0.592479 0.262896 0.021 Uiso 1 1 calc R U . . .
H3'B H 0.874217 0.497223 0.223893 0.021 Uiso 1 1 calc R U . . .
C7 C 0.5130(7) 0.7086(6) 0.1577(3) 0.0157(13) Uani 1 1 d . . . . .
H7 H 0.452019 0.772350 0.192356 0.019 Uiso 1 1 calc R U . . .
C16 C 0.5809(7) 0.1539(6) 0.1649(3) 0.0133(12) Uani 1 1 d . . . . .
C9' C 0.9154(6) 0.7316(6) 0.3533(3) 0.0096(11) Uani 1 1 d . . . . .
C6 C 0.6545(7) 0.7484(7) 0.1206(3) 0.0178(13) Uani 1 1 d . . . . .
H6 H 0.689780 0.839725 0.129692 0.021 Uiso 1 1 calc R U . . .
C11 C 0.7329(7) 0.1628(6) 0.1614(3) 0.0115(12) Uani 1 1 d . . . . .
C8 C 0.4617(7) 0.5735(6) 0.1433(3) 0.0122(8) Uani 1 1 d . . . . .
H8 H 0.365110 0.546661 0.167771 0.015 Uiso 1 1 calc R U . . .
C12 C 0.7938(7) 0.0895(6) 0.2144(3) 0.0157(12) Uani 1 1 d . . . . .
H12 H 0.896557 0.093641 0.211456 0.019 Uiso 1 1 calc R U . . .
C14 C 0.5574(7) 0.0009(6) 0.2753(4) 0.0190(14) Uani 1 1 d . . . . .
H14 H 0.497851 -0.053714 0.314405 0.023 Uiso 1 1 calc R U . . .
C12' C 0.4066(7) 0.4996(7) 0.3468(4) 0.0167(13) Uani 1 1 d . . . . .
H12' H 0.391810 0.422079 0.315520 0.020 Uiso 1 1 calc R U . . .
C15 C 0.4946(7) 0.0716(6) 0.2217(3) 0.0138(12) Uani 1 1 d . . . . .
H15 H 0.392418 0.063677 0.223779 0.017 Uiso 1 1 calc R U . . .
C1' C 0.7155(7) 0.8551(7) 0.5135(3) 0.0152(12) Uani 1 1 d . . . . .
C10 C 0.8294(6) 0.2592(6) 0.1045(3) 0.0128(12) Uani 1 1 d . . . . .
H10A H 0.831703 0.354632 0.127562 0.015 Uiso 1 1 calc R U . . .
H10B H 0.931019 0.219602 0.092483 0.015 Uiso 1 1 calc R U . . .
C1 C 0.2498(6) 0.2857(6) 0.1606(3) 0.0123(12) Uani 1 1 d . . . . .
C2 C 0.8199(9) 0.0465(7) -0.0217(4) 0.0282(17) Uani 1 1 d . . . . .
H2A H 0.882521 -0.009836 -0.062455 0.042 Uiso 1 1 calc R U . . .
H2B H 0.718479 0.047148 -0.028492 0.042 Uiso 1 1 calc R U . . .
H2C H 0.823331 0.004023 0.027749 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5513(6) 0.4785(6) 0.0935(3) 0.0122(8) Uani 1 1 d . . . . .
C5 C 0.7427(7) 0.6548(6) 0.0709(4) 0.0149(12) Uani 1 1 d . . . . .
H5 H 0.838974 0.682083 0.046278 0.018 Uiso 1 1 calc R U . . .
C4' C 0.9279(6) 0.6710(6) 0.2820(3) 0.0126(12) Uani 1 1 d . . . . .
C7' C 1.1008(7) 0.8998(7) 0.2992(4) 0.0200(14) Uani 1 1 d . . . . .
H7' H 1.159856 0.978517 0.305498 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6918(6) 0.5189(6) 0.0561(3) 0.0119(12) Uani 1 1 d . . . . .
C10' C 0.6515(7) 0.3895(6) 0.3479(3) 0.0151(13) Uani 1 1 d . . . . .
H10C H 0.642100 0.314955 0.387641 0.018 Uiso 1 1 calc R U . . .
H10D H 0.637681 0.344735 0.300261 0.018 Uiso 1 1 calc R U . . .
C2' C 0.9588(9) 0.2950(8) 0.3798(4) 0.0314(17) Uani 1 1 d . . . . .
H2'A H 0.875287 0.267165 0.420119 0.047 Uiso 1 1 calc R U . . .
H2'B H 1.010674 0.373002 0.398077 0.047 Uiso 1 1 calc R U . . .
H2'C H 1.026065 0.213131 0.365868 0.047 Uiso 1 1 calc R U . . .
C14' C 0.3205(7) 0.7148(7) 0.4133(4) 0.0177(13) Uani 1 1 d . . . . .
H14' H 0.245289 0.785178 0.428777 0.021 Uiso 1 1 calc R U . . .
C16' C 0.5597(7) 0.6200(6) 0.4178(3) 0.0132(12) Uani 1 1 d . . . . .
C3 C 0.7903(6) 0.4183(6) 0.0028(3) 0.0129(12) Uani 1 1 d . . . . .
H3A H 0.763664 0.420448 -0.047521 0.015 Uiso 1 1 calc R U . . .
H3B H 0.893529 0.448551 -0.004174 0.015 Uiso 1 1 calc R U . . .
C13 C 0.7073(7) 0.0106(6) 0.2714(3) 0.0179(13) Uani 1 1 d . . . . .
H13 H 0.750317 -0.037048 0.308019 0.021 Uiso 1 1 calc R U . . .
C11' C 0.5364(7) 0.5061(6) 0.3729(3) 0.0135(12) Uani 1 1 d . . . . .
C6' C 1.1144(7) 0.8395(7) 0.2279(4) 0.0186(13) Uani 1 1 d . . . . .
H6' H 1.182512 0.876046 0.185304 0.022 Uiso 1 1 calc R U . . .
C8' C 1.0030(6) 0.8473(6) 0.3611(3) 0.0132(12) Uani 1 1 d . . . . .
H8' H 0.994945 0.890107 0.409673 0.016 Uiso 1 1 calc R U . . .
C13' C 0.2981(7) 0.6057(7) 0.3661(4) 0.0183(13) Uani 1 1 d . . . . .
H13' H 0.210720 0.602824 0.347236 0.022 Uiso 1 1 calc R U . . .
C5' C 1.0265(7) 0.7240(7) 0.2194(4) 0.0178(13) Uani 1 1 d . . . . .
H5' H 1.034356 0.681756 0.170678 0.021 Uiso 1 1 calc R U . . .
C15' C 0.4507(7) 0.7246(6) 0.4389(3) 0.0145(12) Uani 1 1 d . . . . .
H15' H 0.464772 0.801946 0.470474 0.017 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N1 2.694(5) . ?
Bi1 C16 2.254(6) . ?
Bi1 C1 2.387(6) . ?
Bi1 C9 2.255(6) . ?
Bi1' N1' 2.695(5) . ?
Bi1' C9' 2.266(6) . ?
Bi1' C1' 2.368(6) . ?
Bi1' C16' 2.264(6) . ?
F2' C1' 1.356(7) . ?
O1 N1 1.442(6) . ?
O1 C2 1.407(7) . ?
F1 C1 1.370(6) . ?
N1 C10 1.480(7) . ?
N1 C3 1.455(7) . ?
F2 C1 1.334(7) . ?
F3 C1 1.365(7) . ?
F3' C1' 1.385(7) . ?
N1' O1' 1.443(6) . ?
N1' C3' 1.462(8) . ?
N1' C10' 1.484(8) . ?
O1' C2' 1.404(8) . ?
F1' C1' 1.340(7) . ?
C3' H3'A 0.9900 . ?
C3' H3'B 0.9900 . ?
C3' C4' 1.515(8) . ?
C7 H7 0.9500 . ?
C7 C6 1.399(9) . ?
C7 C8 1.407(8) . ?
C16 C11 1.409(8) . ?
C16 C15 1.395(8) . ?
C9' C4' 1.384(8) . ?
C9' C8' 1.395(8) . ?
C6 H6 0.9500 . ?
C6 C5 1.378(9) . ?
C11 C12 1.387(8) . ?
C11 C10 1.516(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(9) . ?
C14 C13 1.389(9) . ?
C12' H12' 0.9500 . ?
C12' C11' 1.393(8) . ?
C12' C13' 1.394(9) . ?
C15 H15 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C9 C4 1.394(8) . ?
C5 H5 0.9500 . ?
C5 C4 1.414(8) . ?
C4' C5' 1.387(8) . ?
C7' H7' 0.9500 . ?
C7' C6' 1.382(9) . ?
C7' C8' 1.372(9) . ?
C4 C3 1.496(8) . ?
C10' H10C 0.9900 . ?
C10' H10D 0.9900 . ?
C10' C11' 1.515(8) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C14' H14' 0.9500 . ?
C14' C13' 1.378(9) . ?
C14' C15' 1.394(9) . ?
C16' C11' 1.389(8) . ?
C16' C15' 1.391(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C13 H13 0.9500 . ?
C6' H6' 0.9500 . ?
C6' C5' 1.399(9) . ?
C8' H8' 0.9500 . ?
C13' H13' 0.9500 . ?
C5' H5' 0.9500 . ?
C15' H15' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 Bi1 N1 71.01(18) . . ?
C16 Bi1 C1 91.4(2) . . ?
C16 Bi1 C9 95.3(2) . . ?
C1 Bi1 N1 153.21(17) . . ?
C9 Bi1 N1 69.68(18) . . ?
C9 Bi1 C1 92.9(2) . . ?
C9' Bi1' N1' 70.49(18) . . ?
C9' Bi1' C1' 89.8(2) . . ?
C1' Bi1' N1' 149.43(18) . . ?
C16' Bi1' N1' 69.11(19) . . ?
C16' Bi1' C9' 99.1(2) . . ?
C16' Bi1' C1' 92.3(2) . . ?
C2 O1 N1 110.6(4) . . ?
O1 N1 Bi1 125.1(3) . . ?
O1 N1 C10 107.8(4) . . ?
O1 N1 C3 104.9(4) . . ?
C10 N1 Bi1 105.8(3) . . ?
C3 N1 Bi1 100.5(3) . . ?
C3 N1 C10 112.7(4) . . ?
O1' N1' Bi1' 124.5(3) . . ?
O1' N1' C3' 105.1(4) . . ?
O1' N1' C10' 107.9(4) . . ?
C3' N1' Bi1' 103.8(3) . . ?
C3' N1' C10' 112.9(5) . . ?
C10' N1' Bi1' 102.7(3) . . ?
C2' O1' N1' 111.1(5) . . ?
N1' C3' H3'A 109.2 . . ?
N1' C3' H3'B 109.2 . . ?
N1' C3' C4' 111.9(5) . . ?
H3'A C3' H3'B 107.9 . . ?
C4' C3' H3'A 109.2 . . ?
C4' C3' H3'B 109.2 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.5(6) . . ?
C8 C7 H7 120.3 . . ?
C11 C16 Bi1 120.4(4) . . ?
C15 C16 Bi1 120.1(4) . . ?
C15 C16 C11 119.3(5) . . ?
C4' C9' Bi1' 119.9(4) . . ?
C4' C9' C8' 119.0(5) . . ?
C8' C9' Bi1' 120.8(4) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.9(6) . . ?
C5 C6 H6 120.1 . . ?
C16 C11 C10 121.3(5) . . ?
C12 C11 C16 119.4(5) . . ?
C12 C11 C10 119.2(5) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(6) . . ?
C9 C8 H8 119.7 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(6) . . ?
C13 C12 H12 119.5 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(6) . . ?
C11' C12' H12' 119.7 . . ?
C11' C12' C13' 120.7(6) . . ?
C13' C12' H12' 119.7 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.5(6) . . ?
C14 C15 H15 119.8 . . ?
F2' C1' Bi1' 118.2(4) . . ?
F2' C1' F3' 103.8(5) . . ?
F3' C1' Bi1' 110.2(4) . . ?
F1' C1' Bi1' 113.5(4) . . ?
F1' C1' F2' 106.0(5) . . ?
F1' C1' F3' 103.7(5) . . ?
N1 C10 C11 112.1(5) . . ?
N1 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
F1 C1 Bi1 108.7(4) . . ?
F2 C1 Bi1 120.1(4) . . ?
F2 C1 F1 104.9(5) . . ?
F2 C1 F3 105.5(5) . . ?
F3 C1 Bi1 112.1(4) . . ?
F3 C1 F1 104.3(4) . . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
O1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C9 Bi1 122.4(4) . . ?
C8 C9 C4 119.8(5) . . ?
C4 C9 Bi1 117.8(4) . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 121.0(6) . . ?
C4 C5 H5 119.5 . . ?
C9' C4' C3' 120.4(5) . . ?
C9' C4' C5' 120.5(6) . . ?
C5' C4' C3' 118.9(5) . . ?
C6' C7' H7' 119.6 . . ?
C8' C7' H7' 119.6 . . ?
C8' C7' C6' 120.7(6) . . ?
C9 C4 C5 119.3(5) . . ?
C9 C4 C3 120.7(5) . . ?
C5 C4 C3 120.0(5) . . ?
N1' C10' H10C 110.0 . . ?
N1' C10' H10D 110.0 . . ?
N1' C10' C11' 108.5(5) . . ?
H10C C10' H10D 108.4 . . ?
C11' C10' H10C 110.0 . . ?
C11' C10' H10D 110.0 . . ?
O1' C2' H2'A 109.5 . . ?
O1' C2' H2'B 109.5 . . ?
O1' C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C13' C14' H14' 119.2 . . ?
C13' C14' C15' 121.7(6) . . ?
C15' C14' H14' 119.2 . . ?
C11' C16' Bi1' 118.6(4) . . ?
C11' C16' C15' 119.7(6) . . ?
C15' C16' Bi1' 121.6(4) . . ?
N1 C3 C4 110.2(5) . . ?
N1 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C12 C13 C14 120.1(6) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12' C11' C10' 118.0(5) . . ?
C16' C11' C12' 120.0(6) . . ?
C16' C11' C10' 121.9(6) . . ?
C7' C6' H6' 120.5 . . ?
C7' C6' C5' 119.1(6) . . ?
C5' C6' H6' 120.5 . . ?
C9' C8' H8' 119.7 . . ?
C7' C8' C9' 120.7(6) . . ?
C7' C8' H8' 119.7 . . ?
C12' C13' H13' 120.8 . . ?
C14' C13' C12' 118.5(6) . . ?
C14' C13' H13' 120.8 . . ?
C4' C5' C6' 120.0(6) . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C14' C15' H15' 120.3 . . ?
C16' C15' C14' 119.3(6) . . ?
C16' C15' H15' 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C10 C11 32.0(5) . . . . ?
Bi1 N1 C3 C4 46.8(5) . . . . ?
Bi1 C16 C11 C12 -174.6(4) . . . . ?
Bi1 C16 C11 C10 9.9(7) . . . . ?
Bi1 C16 C15 C14 175.8(4) . . . . ?
Bi1 C9 C4 C5 -176.0(4) . . . . ?
Bi1 C9 C4 C3 2.1(7) . . . . ?
Bi1' N1' O1' C2' 23.1(6) . . . . ?
Bi1' N1' C3' C4' 38.2(5) . . . . ?
Bi1' N1' C10' C11' 43.8(5) . . . . ?
Bi1' C9' C4' C3' 10.9(7) . . . . ?
Bi1' C9' C4' C5' -172.7(4) . . . . ?
Bi1' C9' C8' C7' 172.5(4) . . . . ?
Bi1' C16' C11' C12' -179.0(4) . . . . ?
Bi1' C16' C11' C10' -1.7(7) . . . . ?
Bi1' C16' C15' C14' -179.9(4) . . . . ?
O1 N1 C10 C11 -103.9(5) . . . . ?
O1 N1 C3 C4 177.7(5) . . . . ?
N1' C3' C4' C9' -37.5(8) . . . . ?
N1' C3' C4' C5' 146.0(6) . . . . ?
N1' C10' C11' C12' 143.1(5) . . . . ?
N1' C10' C11' C16' -34.2(7) . . . . ?
O1' N1' C3' C4' -93.9(6) . . . . ?
O1' N1' C10' C11' 176.9(4) . . . . ?
C3' N1' O1' C2' 142.2(5) . . . . ?
C3' N1' C10' C11' -67.4(6) . . . . ?
C3' C4' C5' C6' 176.6(6) . . . . ?
C7 C6 C5 C4 0.6(9) . . . . ?
C7 C8 C9 Bi1 175.9(4) . . . . ?
C7 C8 C9 C4 -1.5(9) . . . . ?
C16 C11 C12 C13 -1.4(8) . . . . ?
C16 C11 C10 N1 -31.5(7) . . . . ?
C9' C4' C5' C6' 0.1(9) . . . . ?
C6 C7 C8 C9 1.0(9) . . . . ?
C6 C5 C4 C9 -1.1(9) . . . . ?
C6 C5 C4 C3 -179.1(6) . . . . ?
C11 C16 C15 C14 1.2(9) . . . . ?
C11 C12 C13 C14 1.5(9) . . . . ?
C8 C7 C6 C5 -0.5(9) . . . . ?
C8 C9 C4 C5 1.5(9) . . . . ?
C8 C9 C4 C3 179.5(5) . . . . ?
C12 C11 C10 N1 152.9(5) . . . . ?
C15 C16 C11 C12 0.1(8) . . . . ?
C15 C16 C11 C10 -175.5(5) . . . . ?
C15 C14 C13 C12 -0.3(9) . . . . ?
C10 N1 C3 C4 -65.4(6) . . . . ?
C10 C11 C12 C13 174.3(5) . . . . ?
C2 O1 N1 Bi1 -37.8(6) . . . . ?
C2 O1 N1 C10 87.2(6) . . . . ?
C2 O1 N1 C3 -152.5(5) . . . . ?
C9 C4 C3 N1 -39.6(8) . . . . ?
C5 C4 C3 N1 138.5(5) . . . . ?
C4' C9' C8' C7' -0.4(9) . . . . ?
C7' C6' C5' C4' -0.3(9) . . . . ?
C10' N1' O1' C2' -97.1(6) . . . . ?
C10' N1' C3' C4' 148.7(5) . . . . ?
C3 N1 C10 C11 140.9(5) . . . . ?
C13 C14 C15 C16 -1.1(9) . . . . ?
C11' C12' C13' C14' -1.8(9) . . . . ?
C11' C16' C15' C14' -1.3(9) . . . . ?
C6' C7' C8' C9' 0.1(9) . . . . ?
C8' C9' C4' C3' -176.2(5) . . . . ?
C8' C9' C4' C5' 0.3(9) . . . . ?
C8' C7' C6' C5' 0.2(9) . . . . ?
C13' C12' C11' C10' -178.3(5) . . . . ?
C13' C12' C11' C16' -0.9(9) . . . . ?
C13' C14' C15' C16' -1.4(9) . . . . ?
C15' C14' C13' C12' 3.0(9) . . . . ?
C15' C16' C11' C12' 2.4(9) . . . . ?
C15' C16' C11' C10' 179.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl101_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2504525'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;Department of Chemistry, University of California, San Diego
United States of America
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Bi F N O'
_chemical_formula_sum            'C15 H15 Bi F N O'
_chemical_formula_weight         453.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.847(2)
_cell_length_b                   14.652(3)
_cell_length_c                   9.803(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.388(8)
_cell_angle_gamma                90
_cell_volume                     1369.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6088
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.098
_cell_measurement_theta_min      2.546
_shelx_estimated_absorpt_T_max   0.332
_shelx_estimated_absorpt_T_min   0.113
_exptl_absorpt_coefficient_mu    12.872
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1335 before and 0.0864 after correction.
The Ratio of minimum to maximum transmission is 0.4989.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4678
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.096
_diffrn_reflns_theta_min         2.135
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2493
_reflns_number_total             2861
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.445
_refine_diff_density_min         -1.506
_refine_diff_density_rms         0.304
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.32175(3) 0.73950(2) 0.81998(3) 0.01123(13) Uani 1 1 d . . . . .
F1 F 0.3202(4) 0.8761(3) 0.7470(5) 0.0186(10) Uani 1 1 d . . . . .
O1 O 0.2809(5) 0.4930(3) 0.8477(5) 0.0152(11) Uani 1 1 d . . . . .
N1 N 0.3386(6) 0.5632(4) 0.7735(6) 0.0113(12) Uani 1 1 d . . . . .
C1 C 0.1620(7) 0.7029(5) 0.6190(7) 0.0124(14) Uani 1 1 d . . . . .
C2 C 0.0671(8) 0.7712(5) 0.5542(9) 0.0137(16) Uani 1 1 d . . . . .
H2 H 0.068499 0.830021 0.595211 0.016 Uiso 1 1 calc R U . . .
C3 C -0.0298(8) 0.7495(5) 0.4271(9) 0.0151(17) Uani 1 1 d . . . . .
H3 H -0.094737 0.794360 0.380730 0.018 Uiso 1 1 calc R U . . .
C4 C -0.0315(7) 0.6632(6) 0.3686(8) 0.0216(18) Uani 1 1 d . . . . .
H4 H -0.097932 0.649030 0.283034 0.026 Uiso 1 1 calc R U . . .
C5 C 0.0641(7) 0.5973(5) 0.4351(7) 0.0141(15) Uani 1 1 d . . . . .
H5 H 0.061998 0.537961 0.395643 0.017 Uiso 1 1 calc R U . . .
C6 C 0.1631(7) 0.6185(5) 0.5599(7) 0.0101(14) Uani 1 1 d . . . . .
C7 C 0.2757(7) 0.5481(5) 0.6215(7) 0.0156(16) Uani 1 1 d . . . . .
H7A H 0.233852 0.486319 0.607871 0.019 Uiso 1 1 calc R U . . .
H7B H 0.350327 0.551011 0.570111 0.019 Uiso 1 1 calc R U . . .
C8 C 0.4935(7) 0.5475(5) 0.8081(8) 0.0141(15) Uani 1 1 d . . . . .
H8A H 0.513978 0.486909 0.773234 0.017 Uiso 1 1 calc R U . . .
H8B H 0.532667 0.549349 0.911327 0.017 Uiso 1 1 calc R U . . .
C9 C 0.5581(7) 0.6212(5) 0.7386(7) 0.0111(14) Uani 1 1 d . . . . .
C10 C 0.6692(7) 0.5983(6) 0.6818(7) 0.0172(17) Uani 1 1 d . . . . .
H10 H 0.703412 0.537382 0.688397 0.021 Uiso 1 1 calc R U . . .
C11 C 0.7308(7) 0.6652(5) 0.6148(8) 0.0178(16) Uani 1 1 d . . . . .
H11 H 0.807598 0.650095 0.576447 0.021 Uiso 1 1 calc R U . . .
C12 C 0.6788(9) 0.7541(5) 0.6045(9) 0.0160(17) Uani 1 1 d . . . . .
H12 H 0.718390 0.799422 0.556933 0.019 Uiso 1 1 calc R U . . .
C13 C 0.5695(7) 0.7762(5) 0.6637(8) 0.0141(15) Uani 1 1 d . . . . .
H13 H 0.535950 0.837161 0.658721 0.017 Uiso 1 1 calc R U . . .
C14 C 0.5072(7) 0.7086(5) 0.7317(7) 0.0131(14) Uani 1 1 d . . . . .
C15 C 0.1922(8) 0.5332(5) 0.9253(8) 0.0210(18) Uani 1 1 d . . . . .
H15A H 0.117301 0.567446 0.861195 0.032 Uiso 1 1 calc R U . . .
H15B H 0.247214 0.574730 0.996356 0.032 Uiso 1 1 calc R U . . .
H15C H 0.150992 0.485250 0.971993 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 F1 2.124(4) . ?
Bi1 N1 2.635(6) . ?
Bi1 C1 2.259(7) . ?
Bi1 C14 2.252(8) . ?
O1 N1 1.454(7) . ?
O1 C15 1.421(8) . ?
N1 C7 1.481(8) . ?
N1 C8 1.496(8) . ?
C1 C2 1.407(10) . ?
C1 C6 1.367(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.405(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(9) . ?
C6 C7 1.524(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.500(10) . ?
C9 C10 1.387(10) . ?
C9 C14 1.371(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.415(11) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 Bi1 N1 149.43(18) . . ?
F1 Bi1 C1 89.1(2) . . ?
F1 Bi1 C14 89.9(2) . . ?
C1 Bi1 N1 71.1(2) . . ?
C14 Bi1 N1 69.2(2) . . ?
C14 Bi1 C1 94.2(2) . . ?
C15 O1 N1 110.0(5) . . ?
O1 N1 Bi1 123.9(4) . . ?
O1 N1 C7 106.3(5) . . ?
O1 N1 C8 106.3(5) . . ?
C7 N1 Bi1 106.9(4) . . ?
C7 N1 C8 110.6(6) . . ?
C8 N1 Bi1 102.5(4) . . ?
C2 C1 Bi1 117.7(5) . . ?
C6 C1 Bi1 120.4(5) . . ?
C6 C1 C2 121.8(7) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 117.9(7) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(7) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(7) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(7) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.6(6) . . ?
C1 C6 C7 121.8(6) . . ?
C5 C6 C7 118.5(6) . . ?
N1 C7 C6 112.2(6) . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
N1 C8 C9 108.1(5) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C10 C9 C8 118.3(7) . . ?
C14 C9 C8 120.3(7) . . ?
C14 C9 C10 121.5(7) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(8) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(8) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(7) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.5(7) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 Bi1 119.3(6) . . ?
C9 C14 C13 118.7(7) . . ?
C13 C14 Bi1 121.9(6) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C7 C6 -28.8(6) . . . . ?
Bi1 N1 C8 C9 -46.2(6) . . . . ?
Bi1 C1 C2 C3 178.2(6) . . . . ?
Bi1 C1 C6 C5 -179.6(5) . . . . ?
Bi1 C1 C6 C7 -3.5(9) . . . . ?
O1 N1 C7 C6 105.3(6) . . . . ?
O1 N1 C8 C9 -177.6(5) . . . . ?
N1 C8 C9 C10 -142.2(6) . . . . ?
N1 C8 C9 C14 37.6(9) . . . . ?
C1 C2 C3 C4 0.4(12) . . . . ?
C1 C6 C7 N1 24.8(10) . . . . ?
C2 C1 C6 C5 -2.8(11) . . . . ?
C2 C1 C6 C7 173.3(7) . . . . ?
C2 C3 C4 C5 -0.6(12) . . . . ?
C3 C4 C5 C6 -0.9(11) . . . . ?
C4 C5 C6 C1 2.5(11) . . . . ?
C4 C5 C6 C7 -173.7(7) . . . . ?
C5 C6 C7 N1 -159.1(6) . . . . ?
C6 C1 C2 C3 1.3(11) . . . . ?
C7 N1 C8 C9 67.5(7) . . . . ?
C8 N1 C7 C6 -139.7(6) . . . . ?
C8 C9 C10 C11 179.3(6) . . . . ?
C8 C9 C14 Bi1 -1.8(8) . . . . ?
C8 C9 C14 C13 -179.2(6) . . . . ?
C9 C10 C11 C12 -0.6(10) . . . . ?
C10 C9 C14 Bi1 178.0(5) . . . . ?
C10 C9 C14 C13 0.6(10) . . . . ?
C10 C11 C12 C13 1.7(11) . . . . ?
C11 C12 C13 C14 -1.7(11) . . . . ?
C12 C13 C14 Bi1 -176.8(6) . . . . ?
C12 C13 C14 C9 0.5(10) . . . . ?
C14 C9 C10 C11 -0.5(10) . . . . ?
C15 O1 N1 Bi1 11.6(6) . . . . ?
C15 O1 N1 C7 -112.6(6) . . . . ?
C15 O1 N1 C8 129.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl100_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2504524'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;Department of Chemistry, University of California, San Diego
United States of America
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 Bi F S'
_chemical_formula_sum            'C14 H12 Bi F S'
_chemical_formula_weight         440.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7248(7)
_cell_length_b                   8.8059(5)
_cell_length_c                   12.0826(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.804(2)
_cell_angle_gamma                90
_cell_volume                     1241.10(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6708
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.212
_cell_measurement_theta_min      2.553
_shelx_estimated_absorpt_T_max   0.144
_shelx_estimated_absorpt_T_min   0.103
_exptl_absorpt_coefficient_mu    14.359
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1448 before and 0.0855 after correction.
The Ratio of minimum to maximum transmission is 0.4311.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11106
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.224
_diffrn_reflns_theta_min         2.307
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2580
_reflns_number_total             2772
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.236
_refine_diff_density_min         -1.212
_refine_diff_density_rms         0.238
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+4.1286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.32757(2) 0.68017(2) 0.80467(2) 0.01100(10) Uani 1 1 d . . . . .
S1 S 0.54419(12) 0.83369(14) 0.83610(12) 0.0148(3) Uani 1 1 d . . . . .
F1 F 0.2090(3) 0.5040(4) 0.7429(3) 0.0182(7) Uani 1 1 d . . . . .
C1 C 0.3837(5) 0.6980(6) 0.6324(4) 0.0124(10) Uani 1 1 d . . . . .
C2 C 0.3331(4) 0.6042(6) 0.5484(4) 0.0145(10) Uani 1 1 d . . . . .
H2 H 0.272278 0.538298 0.563128 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3712(5) 0.6067(6) 0.4429(4) 0.0169(11) Uani 1 1 d . . . . .
H3 H 0.335510 0.543389 0.385901 0.020 Uiso 1 1 calc R U . . .
C4 C 0.4616(5) 0.7018(7) 0.4202(5) 0.0187(12) Uani 1 1 d . . . . .
H4 H 0.488740 0.702052 0.348780 0.022 Uiso 1 1 calc R U . . .
C5 C 0.5108(5) 0.7959(6) 0.5042(5) 0.0164(11) Uani 1 1 d . . . . .
H5 H 0.571712 0.861611 0.489401 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4726(5) 0.7958(6) 0.6098(5) 0.0137(11) Uani 1 1 d . . . . .
C7 C 0.5233(4) 0.9093(6) 0.6962(4) 0.0135(10) Uani 1 1 d . . . . .
H7A H 0.471895 0.998542 0.695774 0.016 Uiso 1 1 calc R U . . .
H7B H 0.598107 0.944807 0.674691 0.016 Uiso 1 1 calc R U . . .
C8 C 0.6310(5) 0.6653(6) 0.8186(6) 0.0180(12) Uani 1 1 d . . . . .
H8A H 0.647134 0.659378 0.739829 0.022 Uiso 1 1 calc R U . . .
H8B H 0.705298 0.677358 0.864478 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5770(4) 0.5165(6) 0.8498(4) 0.0121(10) Uani 1 1 d . . . . .
C10 C 0.6501(5) 0.3945(6) 0.8753(5) 0.0173(11) Uani 1 1 d . . . . .
H10 H 0.730530 0.409441 0.877819 0.021 Uiso 1 1 calc R U . . .
C11 C 0.6084(5) 0.2511(7) 0.8972(4) 0.0170(11) Uani 1 1 d . . . . .
H11 H 0.659502 0.168588 0.913625 0.020 Uiso 1 1 calc R U . . .
C12 C 0.4918(5) 0.2308(6) 0.8948(4) 0.0152(11) Uani 1 1 d . . . . .
H12 H 0.462093 0.132920 0.908164 0.018 Uiso 1 1 calc R U . . .
C13 C 0.4174(5) 0.3517(6) 0.8729(4) 0.0132(10) Uani 1 1 d . . . . .
H13 H 0.337359 0.336748 0.874837 0.016 Uiso 1 1 calc R U . . .
C14 C 0.4586(4) 0.4957(6) 0.8481(4) 0.0105(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 S1 2.8683(14) . ?
Bi1 F1 2.165(3) . ?
Bi1 C1 2.251(5) . ?
Bi1 C14 2.261(5) . ?
S1 C7 1.810(5) . ?
S1 C8 1.823(6) . ?
C1 C2 1.394(7) . ?
C1 C6 1.401(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(8) . ?
C6 C7 1.522(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.520(7) . ?
C9 C10 1.389(7) . ?
C9 C14 1.399(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.400(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 Bi1 S1 155.86(9) . . ?
F1 Bi1 C1 88.20(17) . . ?
F1 Bi1 C14 87.86(16) . . ?
C1 Bi1 S1 75.64(14) . . ?
C1 Bi1 C14 90.55(18) . . ?
C14 Bi1 S1 74.71(13) . . ?
C7 S1 Bi1 90.89(17) . . ?
C7 S1 C8 102.4(3) . . ?
C8 S1 Bi1 95.66(18) . . ?
C2 C1 Bi1 119.3(4) . . ?
C2 C1 C6 119.5(5) . . ?
C6 C1 Bi1 121.1(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(5) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.7(5) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(6) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 121.2(5) . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 C7 119.2(5) . . ?
S1 C7 H7A 108.8 . . ?
S1 C7 H7B 108.8 . . ?
C6 C7 S1 113.9(4) . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
S1 C8 H8A 108.5 . . ?
S1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 S1 114.9(4) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C10 C9 C8 117.4(5) . . ?
C10 C9 C14 119.4(5) . . ?
C14 C9 C8 123.2(5) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(5) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.8(5) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.7(5) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(5) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 Bi1 124.0(4) . . ?
C9 C14 C13 118.6(5) . . ?
C13 C14 Bi1 117.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 S1 C7 C6 -41.4(4) . . . . ?
Bi1 S1 C8 C9 -27.5(4) . . . . ?
Bi1 C1 C2 C3 -176.1(4) . . . . ?
Bi1 C1 C6 C5 175.3(4) . . . . ?
Bi1 C1 C6 C7 -8.6(7) . . . . ?
S1 C8 C9 C10 -158.4(4) . . . . ?
S1 C8 C9 C14 25.1(7) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C1 C6 C7 S1 41.6(6) . . . . ?
C2 C1 C6 C5 -1.3(8) . . . . ?
C2 C1 C6 C7 174.8(5) . . . . ?
C2 C3 C4 C5 -1.4(8) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 C1 0.7(8) . . . . ?
C4 C5 C6 C7 -175.5(5) . . . . ?
C5 C6 C7 S1 -142.3(4) . . . . ?
C6 C1 C2 C3 0.5(8) . . . . ?
C7 S1 C8 C9 -119.7(4) . . . . ?
C8 S1 C7 C6 54.6(4) . . . . ?
C8 C9 C10 C11 -175.4(5) . . . . ?
C8 C9 C14 Bi1 -2.1(7) . . . . ?
C8 C9 C14 C13 176.8(5) . . . . ?
C9 C10 C11 C12 -0.8(8) . . . . ?
C10 C9 C14 Bi1 -178.6(4) . . . . ?
C10 C9 C14 C13 0.3(7) . . . . ?
C10 C11 C12 C13 -1.2(8) . . . . ?
C11 C12 C13 C14 2.8(8) . . . . ?
C12 C13 C14 Bi1 176.7(4) . . . . ?
C12 C13 C14 C9 -2.3(8) . . . . ?
C14 C9 C10 C11 1.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl109
_database_code_depnum_ccdc_archive 'CCDC 2504522'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;Department of Chemistry, University of California, San Diego
United States of America
;
_audit_update_record             
;
2025-11-20 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 Bi F3 N2 O, C3 H3'
_chemical_formula_sum            'C24 H27 Bi F3 N2 O'
_chemical_formula_weight         625.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1393(7)
_cell_length_b                   13.2160(9)
_cell_length_c                   17.0483(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.660(2)
_cell_angle_gamma                90
_cell_volume                     2276.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8912
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.455
_shelx_estimated_absorpt_T_min   0.204
_exptl_absorpt_coefficient_mu    7.786
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0969 before and 0.0863 after correction.
The Ratio of minimum to maximum transmission is 0.5899.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15187
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_min         1.952
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4610
_reflns_number_total             5225
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 v2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT v8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.671
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.223
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C16(H16A,H16B), C18(H18A,H18B), C8(H8A,H8B), C9(H9A,H9B),
 C21(H21A,H21B), C20(H20A,H20B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C23(H23), C24(H24), C15(H15), C4(H4), C13(H13), C3(H3), C14(H14),
 C22(H22), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.33168(2) 0.51614(2) 0.62179(2) 0.01379(8) Uani 1 1 d . . . . .
F1 F 0.1012(3) 0.6771(2) 0.60801(18) 0.0354(7) Uani 1 1 d . . . . .
F2 F 0.2813(3) 0.7632(2) 0.62977(18) 0.0358(7) Uani 1 1 d . . . . .
F3 F 0.2265(3) 0.7021(2) 0.51424(17) 0.0337(7) Uani 1 1 d . . . . .
O1 O -0.0465(3) 0.3284(3) 0.68107(19) 0.0291(8) Uani 1 1 d . . . . .
N1 N 0.5151(3) 0.4028(3) 0.6908(2) 0.0166(7) Uani 1 1 d . . . . .
N2 N 0.2339(3) 0.3306(3) 0.7192(2) 0.0168(7) Uani 1 1 d . . . . .
C11 C 0.3487(4) 0.5586(3) 0.7504(2) 0.0145(8) Uani 1 1 d . . . . .
C17 C 0.3576(4) 0.2875(3) 0.7552(3) 0.0199(9) Uani 1 1 d . . . . .
H17A H 0.343327 0.215025 0.766372 0.024 Uiso 1 1 calc R U . . .
H17B H 0.380914 0.321931 0.806002 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4524(5) 0.5165(3) 0.7981(3) 0.0162(10) Uani 1 1 d . . . . .
C2 C 0.5314(4) 0.5771(3) 0.5924(2) 0.0183(9) Uani 1 1 d . . . . .
C12 C 0.2529(4) 0.6160(3) 0.7845(2) 0.0182(9) Uani 1 1 d . . . . .
H12 H 0.181246 0.643853 0.752142 0.022 Uiso 1 1 calc R U . . .
C16 C 0.4736(4) 0.2972(3) 0.7038(3) 0.0224(10) Uani 1 1 d . . . . .
H16A H 0.549966 0.259202 0.728884 0.027 Uiso 1 1 calc R U . . .
H16B H 0.448692 0.265446 0.652143 0.027 Uiso 1 1 calc R U . . .
C23 C 0.0987(6) 0.9541(5) 0.5488(3) 0.0356(13) Uani 1 1 d . . . . .
H23 H 0.166561 0.922769 0.582076 0.043 Uiso 1 1 calc R U . . .
C18 C 0.1393(4) 0.3476(4) 0.7792(3) 0.0216(9) Uani 1 1 d . . . . .
H18A H 0.178908 0.393852 0.820327 0.026 Uiso 1 1 calc R U . . .
H18B H 0.119693 0.282541 0.804598 0.026 Uiso 1 1 calc R U . . .
C24 C 0.1191(6) 1.0489(5) 0.5179(3) 0.0365(13) Uani 1 1 d . . . . .
H24 H 0.200842 1.082601 0.530355 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4613(5) 0.5345(4) 0.8800(3) 0.0214(9) Uani 1 1 d . . . . .
H15 H 0.532924 0.507231 0.912721 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6790(5) 0.7033(4) 0.5453(3) 0.0294(12) Uani 1 1 d . . . . .
H4 H 0.692856 0.768730 0.524529 0.035 Uiso 1 1 calc R U . . .
C1 C 0.2306(5) 0.6773(3) 0.5924(3) 0.0223(9) Uani 1 1 d . . . . .
C13 C 0.2613(5) 0.6328(3) 0.8656(3) 0.0228(10) Uani 1 1 d . . . . .
H13 H 0.195929 0.672004 0.888496 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5530(5) 0.6727(4) 0.5616(2) 0.0229(10) Uani 1 1 d . . . . .
H3 H 0.480492 0.717737 0.551581 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6186(4) 0.4046(4) 0.6346(3) 0.0198(9) Uani 1 1 d . . . . .
H8A H 0.592443 0.359479 0.589689 0.024 Uiso 1 1 calc R U . . .
H8B H 0.702656 0.378938 0.660866 0.024 Uiso 1 1 calc R U . . .
C9 C 0.5615(4) 0.4554(4) 0.7637(3) 0.0173(8) Uani 1 1 d . . . . .
H9A H 0.634947 0.501399 0.752905 0.021 Uiso 1 1 calc R U . . .
H9B H 0.596447 0.404984 0.803034 0.021 Uiso 1 1 calc R U . . .
C21 C 0.1713(5) 0.2649(4) 0.6581(3) 0.0223(10) Uani 1 1 d . . . . .
H21A H 0.152685 0.198057 0.680953 0.027 Uiso 1 1 calc R U . . .
H21B H 0.232398 0.254508 0.616323 0.027 Uiso 1 1 calc R U . . .
C20 C 0.0436(5) 0.3112(4) 0.6226(3) 0.0271(11) Uani 1 1 d . . . . .
H20A H 0.063025 0.376233 0.597054 0.033 Uiso 1 1 calc R U . . .
H20B H 0.002326 0.265407 0.581719 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3658(5) 0.5918(4) 0.9123(3) 0.0239(10) Uani 1 1 d . . . . .
H14 H 0.371834 0.603363 0.967446 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6392(5) 0.5111(3) 0.6046(3) 0.0208(10) Uani 1 1 d . . . . .
C22 C -0.0214(6) 0.9045(4) 0.5313(3) 0.0361(13) Uani 1 1 d . . . . .
H22 H -0.036267 0.839583 0.552745 0.043 Uiso 1 1 calc R U . . .
C19 C 0.0130(5) 0.3929(4) 0.7419(3) 0.0273(11) Uani 1 1 d . . . . .
H19A H -0.049820 0.403257 0.782654 0.033 Uiso 1 1 calc R U . . .
H19B H 0.032273 0.459726 0.719205 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7844(5) 0.6369(4) 0.5598(3) 0.0285(11) Uani 1 1 d . . . . .
H5 H 0.870908 0.657366 0.548935 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7650(5) 0.5425(4) 0.5897(3) 0.0233(10) Uani 1 1 d . . . . .
H6 H 0.838182 0.498324 0.600256 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N1 2.594(3) . ?
Bi1 C11 2.256(4) . ?
Bi1 C2 2.273(4) . ?
Bi1 C1 2.399(5) . ?
F1 C1 1.359(5) . ?
F2 C1 1.380(5) . ?
F3 C1 1.370(5) . ?
O1 C20 1.424(6) . ?
O1 C19 1.437(6) . ?
N1 C16 1.480(6) . ?
N1 C8 1.477(5) . ?
N1 C9 1.468(5) . ?
N2 C17 1.465(5) . ?
N2 C18 1.475(5) . ?
N2 C21 1.462(6) . ?
C11 C10 1.392(6) . ?
C11 C12 1.395(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.528(6) . ?
C10 C15 1.412(7) . ?
C10 C9 1.525(6) . ?
C2 C3 1.393(6) . ?
C2 C7 1.400(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.397(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C23 H23 0.9500 . ?
C23 C24 1.381(8) . ?
C23 C22 1.394(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.507(7) . ?
C24 H24 0.9500 . ?
C24 C22 1.388(9) 3_576 ?
C15 H15 0.9500 . ?
C15 C14 1.380(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.389(7) . ?
C4 C5 1.389(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(7) . ?
C3 H3 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.518(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.514(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C14 H14 0.9500 . ?
C7 C6 1.384(6) . ?
C22 H22 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C6 1.368(7) . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Bi1 N1 73.00(13) . . ?
C11 Bi1 C2 97.29(15) . . ?
C11 Bi1 C1 88.81(15) . . ?
C2 Bi1 N1 71.69(14) . . ?
C2 Bi1 C1 90.72(16) . . ?
C1 Bi1 N1 152.32(14) . . ?
C20 O1 C19 110.1(3) . . ?
C16 N1 Bi1 114.2(3) . . ?
C8 N1 Bi1 102.6(2) . . ?
C8 N1 C16 109.8(3) . . ?
C9 N1 Bi1 106.2(2) . . ?
C9 N1 C16 113.3(3) . . ?
C9 N1 C8 110.2(3) . . ?
C17 N2 C18 110.6(3) . . ?
C21 N2 C17 112.0(4) . . ?
C21 N2 C18 108.4(3) . . ?
C10 C11 Bi1 117.6(3) . . ?
C10 C11 C12 119.5(4) . . ?
C12 C11 Bi1 122.6(3) . . ?
N2 C17 H17A 108.8 . . ?
N2 C17 H17B 108.8 . . ?
N2 C17 C16 113.6(4) . . ?
H17A C17 H17B 107.7 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C11 C10 C15 119.7(4) . . ?
C11 C10 C9 121.6(4) . . ?
C15 C10 C9 118.6(4) . . ?
C3 C2 Bi1 125.1(3) . . ?
C3 C2 C7 118.4(4) . . ?
C7 C2 Bi1 116.5(3) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
N1 C16 C17 114.0(4) . . ?
N1 C16 H16A 108.8 . . ?
N1 C16 H16B 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C22 119.9(6) . . ?
C22 C23 H23 120.0 . . ?
N2 C18 H18A 109.6 . . ?
N2 C18 H18B 109.6 . . ?
N2 C18 C19 110.2(4) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C22 120.8(6) . 3_576 ?
C22 C24 H24 119.6 3_576 . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
F1 C1 Bi1 111.1(3) . . ?
F1 C1 F2 104.0(4) . . ?
F1 C1 F3 103.7(4) . . ?
F2 C1 Bi1 119.8(3) . . ?
F3 C1 Bi1 113.2(3) . . ?
F3 C1 F2 103.5(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.3(4) . . ?
C14 C13 H13 120.3 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.5 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C7 111.0(4) . . ?
H8A C8 H8B 108.0 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
N1 C9 C10 112.5(4) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 C20 110.6(4) . . ?
H21A C21 H21B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
O1 C20 C21 111.2(4) . . ?
O1 C20 H20A 109.4 . . ?
O1 C20 H20B 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C2 C7 C8 120.0(4) . . ?
C6 C7 C2 120.4(5) . . ?
C6 C7 C8 119.6(5) . . ?
C23 C22 H22 120.4 . . ?
C24 C22 C23 119.3(5) 3_576 . ?
C24 C22 H22 120.4 3_576 . ?
O1 C19 C18 111.2(4) . . ?
O1 C19 H19A 109.4 . . ?
O1 C19 H19B 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.3(5) . . ?
C5 C6 H6 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C16 C17 -60.1(4) . . . . ?
Bi1 N1 C8 C7 44.2(4) . . . . ?
Bi1 N1 C9 C10 31.7(4) . . . . ?
Bi1 C11 C10 C15 -175.1(3) . . . . ?
Bi1 C11 C10 C9 8.2(6) . . . . ?
Bi1 C11 C12 C13 174.1(3) . . . . ?
Bi1 C2 C3 C4 -179.9(3) . . . . ?
Bi1 C2 C7 C8 1.0(6) . . . . ?
Bi1 C2 C7 C6 -178.7(4) . . . . ?
N1 C8 C7 C2 -35.3(6) . . . . ?
N1 C8 C7 C6 144.4(4) . . . . ?
N2 C17 C16 N1 65.4(5) . . . . ?
N2 C18 C19 O1 58.5(5) . . . . ?
N2 C21 C20 O1 -58.5(5) . . . . ?
C11 C10 C15 C14 1.5(7) . . . . ?
C11 C10 C9 N1 -30.0(6) . . . . ?
C11 C12 C13 C14 -0.1(7) . . . . ?
C17 N2 C18 C19 179.4(4) . . . . ?
C17 N2 C21 C20 179.6(4) . . . . ?
C10 C11 C12 C13 1.1(7) . . . . ?
C10 C15 C14 C13 -0.5(7) . . . . ?
C2 C7 C6 C5 -2.7(7) . . . . ?
C12 C11 C10 C15 -1.8(7) . . . . ?
C12 C11 C10 C9 -178.4(4) . . . . ?
C12 C13 C14 C15 -0.2(7) . . . . ?
C16 N1 C8 C7 166.0(4) . . . . ?
C16 N1 C9 C10 -94.5(4) . . . . ?
C18 N2 C17 C16 -162.5(4) . . . . ?
C18 N2 C21 C20 57.3(5) . . . . ?
C24 C23 C22 C24 0.5(10) . . . 3_576 ?
C15 C10 C9 N1 153.3(4) . . . . ?
C4 C5 C6 C7 1.1(7) . . . . ?
C3 C2 C7 C8 -177.3(4) . . . . ?
C3 C2 C7 C6 3.0(7) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C8 N1 C16 C17 -174.6(4) . . . . ?
C8 N1 C9 C10 142.1(4) . . . . ?
C8 C7 C6 C5 177.6(4) . . . . ?
C9 N1 C16 C17 61.7(5) . . . . ?
C9 N1 C8 C7 -68.5(5) . . . . ?
C9 C10 C15 C14 178.2(4) . . . . ?
C21 N2 C17 C16 76.4(5) . . . . ?
C21 N2 C18 C19 -57.4(5) . . . . ?
C20 O1 C19 C18 -58.0(5) . . . . ?
C7 C2 C3 C4 -1.7(7) . . . . ?
C22 C23 C24 C22 -0.5(10) . . . 3_576 ?
C19 O1 C20 C21 57.7(5) . . . . ?
C5 C4 C3 C2 0.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl112
_database_code_depnum_ccdc_archive 'CCDC 2504512'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;Department of Chemistry, University of California, San Diego
United States of America
;
_audit_update_record             
;
2025-11-20 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2025-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Bi F3 S'
_chemical_formula_sum            'C15 H12 Bi F3 S'
_chemical_formula_weight         490.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7437(5)
_cell_length_b                   9.1594(5)
_cell_length_c                   10.8034(6)
_cell_angle_alpha                102.249(2)
_cell_angle_beta                 102.9270(10)
_cell_angle_gamma                114.5380(10)
_cell_volume                     720.28(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9288
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.177
_cell_measurement_theta_min      2.060
_shelx_estimated_absorpt_T_max   0.171
_shelx_estimated_absorpt_T_min   0.123
_exptl_absorpt_coefficient_mu    12.402
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9272
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.177
_diffrn_reflns_theta_min         2.060
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3073
_reflns_number_total             3198
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.353
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0186
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0154P)²+0.0864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0439
_refine_ls_wR_factor_ref         0.0443
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.40260(2) 0.47122(2) 0.27456(2) 0.01726(5) Uani 1 1 d . . . . .
S1 S 0.79993(10) 0.70733(10) 0.42639(9) 0.02992(18) Uani 1 1 d . . . . .
F1 F 0.0291(2) 0.2975(3) 0.03260(19) 0.0348(4) Uani 1 1 d . . . . .
F2 F 0.0455(2) 0.5112(3) 0.1759(2) 0.0324(4) Uani 1 1 d . . . . .
F3 F -0.0044(3) 0.2813(3) 0.2223(2) 0.0411(5) Uani 1 1 d . . . . .
C1 C 0.8179(4) 0.7000(4) 0.2609(4) 0.0313(8) Uani 1 1 d . . . . .
H1A H 0.938933 0.789984 0.273746 0.038 Uiso 1 1 calc R U . . .
H1B H 0.807264 0.588316 0.215968 0.038 Uiso 1 1 calc R U . . .
C2 C 0.6803(4) 0.7237(4) 0.1681(3) 0.0218(6) Uani 1 1 d . . . . .
C3 C 0.7384(4) 0.8344(4) 0.0966(3) 0.0302(7) Uani 1 1 d . . . . .
H3 H 0.863091 0.897187 0.112432 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6191(5) 0.8543(4) 0.0039(3) 0.0300(7) Uani 1 1 d . . . . .
H4 H 0.660989 0.928505 -0.044658 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4367(5) 0.7651(4) -0.0182(3) 0.0278(7) Uani 1 1 d . . . . .
H5 H 0.353099 0.776176 -0.083327 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3772(4) 0.6594(4) 0.0557(3) 0.0203(6) Uani 1 1 d . . . . .
H6 H 0.252684 0.600710 0.041574 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4968(3) 0.6378(3) 0.1500(3) 0.0167(5) Uani 1 1 d . . . . .
C8 C 0.4305(4) 0.6832(3) 0.4471(3) 0.0204(6) Uani 1 1 d . . . . .
C9 C 0.2849(4) 0.6534(4) 0.4902(3) 0.0238(6) Uani 1 1 d . . . . .
H9 H 0.173362 0.552213 0.440553 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3008(4) 0.7704(4) 0.6054(3) 0.0263(7) Uani 1 1 d . . . . .
H10 H 0.200723 0.748672 0.633927 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4635(5) 0.9187(4) 0.6782(3) 0.0290(7) Uani 1 1 d . . . . .
H11 H 0.475795 0.997991 0.757437 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6072(4) 0.9503(4) 0.6347(3) 0.0269(7) Uani 1 1 d . . . . .
H12 H 0.717772 1.052616 0.684151 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5934(4) 0.8349(4) 0.5195(3) 0.0228(6) Uani 1 1 d . . . . .
C14 C 0.7532(4) 0.8831(4) 0.4738(3) 0.0264(7) Uani 1 1 d . . . . .
H14A H 0.860174 0.980699 0.547727 0.032 Uiso 1 1 calc R U . . .
H14B H 0.730553 0.920611 0.395339 0.032 Uiso 1 1 calc R U . . .
C15 C 0.0954(4) 0.3891(4) 0.1678(3) 0.0234(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 S1 3.0236(7) . ?
Bi1 C7 2.267(3) . ?
Bi1 C8 2.274(3) . ?
Bi1 C15 2.383(3) . ?
S1 C1 1.819(4) . ?
S1 C14 1.819(3) . ?
F1 C15 1.367(3) . ?
F2 C15 1.353(3) . ?
F3 C15 1.358(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.506(4) . ?
C2 C3 1.402(4) . ?
C2 C7 1.406(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.397(4) . ?
C8 C9 1.394(4) . ?
C8 C13 1.402(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.396(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(4) . ?
C13 C14 1.511(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 Bi1 S1 74.40(7) . . ?
C7 Bi1 C8 95.36(10) . . ?
C7 Bi1 C15 93.03(10) . . ?
C8 Bi1 S1 72.96(8) . . ?
C8 Bi1 C15 90.73(10) . . ?
C15 Bi1 S1 157.99(8) . . ?
C1 S1 Bi1 85.82(10) . . ?
C1 S1 C14 103.41(15) . . ?
C14 S1 Bi1 89.00(10) . . ?
S1 C1 H1A 108.5 . . ?
S1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 S1 115.1(2) . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 C7 119.2(3) . . ?
C7 C2 C1 122.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 Bi1 119.7(2) . . ?
C6 C7 Bi1 121.7(2) . . ?
C6 C7 C2 118.5(3) . . ?
C9 C8 Bi1 118.3(2) . . ?
C9 C8 C13 119.0(3) . . ?
C13 C8 Bi1 122.3(2) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.3(3) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C14 122.4(3) . . ?
C12 C13 C8 119.3(3) . . ?
C12 C13 C14 118.2(3) . . ?
S1 C14 H14A 109.1 . . ?
S1 C14 H14B 109.1 . . ?
C13 C14 S1 112.6(2) . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
F1 C15 Bi1 113.36(18) . . ?
F2 C15 Bi1 119.13(19) . . ?
F2 C15 F1 104.5(2) . . ?
F2 C15 F3 105.5(2) . . ?
F3 C15 Bi1 108.29(19) . . ?
F3 C15 F1 104.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 S1 C1 C2 46.3(2) . . . . ?
Bi1 S1 C14 C13 44.2(2) . . . . ?
Bi1 C8 C9 C10 172.5(2) . . . . ?
Bi1 C8 C13 C12 -172.1(2) . . . . ?
Bi1 C8 C13 C14 11.1(4) . . . . ?
S1 C1 C2 C3 134.8(3) . . . . ?
S1 C1 C2 C7 -45.9(4) . . . . ?
C1 S1 C14 C13 129.7(2) . . . . ?
C1 C2 C3 C4 176.0(3) . . . . ?
C1 C2 C7 Bi1 4.5(4) . . . . ?
C1 C2 C7 C6 -176.1(3) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C3 C2 C7 Bi1 -176.2(2) . . . . ?
C3 C2 C7 C6 3.2(4) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 C7 -1.4(5) . . . . ?
C5 C6 C7 Bi1 178.5(2) . . . . ?
C5 C6 C7 C2 -0.9(4) . . . . ?
C7 C2 C3 C4 -3.4(5) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C8 C13 C14 S1 -47.1(4) . . . . ?
C9 C8 C13 C12 1.5(4) . . . . ?
C9 C8 C13 C14 -175.3(3) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C11 C12 C13 C14 176.5(3) . . . . ?
C12 C13 C14 S1 136.0(2) . . . . ?
C13 C8 C9 C10 -1.4(4) . . . . ?
C14 S1 C1 C2 -41.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl001
_database_code_depnum_ccdc_archive 'CCDC 2504526'
loop_
_audit_author_name
_audit_author_address
'Glenn P. A. Yap'
;University of Delaware
United States of America
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2024-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 Bi F N2 O'
_chemical_formula_sum            'C20 H24 Bi F N2 O'
_chemical_formula_weight         536.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1835(3)
_cell_length_b                   16.0674(6)
_cell_length_c                   14.7898(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.9510(10)
_cell_angle_gamma                90
_cell_volume                     1869.80(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      4.15
_shelx_estimated_absorpt_T_max   0.347
_shelx_estimated_absorpt_T_min   0.245
_exptl_absorpt_coefficient_mu    18.668
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.7081.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3.00 4.00 -4.00 0.0280
-2.00 -1.00 1.00 0.0330
-1.00 4.00 4.00 0.0420
-1.00 -1.00 2.00 0.0350
-1.00 -2.00 1.00 0.0370
-1.00 3.00 0.00 0.0350
-1.00 4.00 -2.00 0.0190
0.00 -4.00 -3.00 0.0380
0.00 -4.00 3.00 0.0350
0.00 -4.00 1.00 0.0310
1.00 -4.00 -4.00 0.0480
1.00 4.00 -1.00 0.0580
1.00 1.00 -2.00 0.0530
1.00 2.00 -1.00 0.0580
1.00 0.00 -4.00 0.0470
1.00 -4.00 -1.00 0.0450
1.00 -1.00 4.00 0.0650
2.00 -1.00 -4.00 0.0570
2.00 -3.00 -3.00 0.0570
4.00 0.00 -1.00 0.0460

_exptl_crystal_size_max          0.105
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.072
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22526
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.237
_diffrn_reflns_theta_min         4.151
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker Venture Photon III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3291
_reflns_number_total             3318
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.00107(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0194
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²+1.7548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0485
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.53463(2) 0.35355(2) 0.50703(2) 0.04188(8) Uani 1 1 d . . . . .
F1 F 0.3817(4) 0.35283(14) 0.60384(16) 0.0712(7) Uani 1 1 d . . . . .
O1 O 1.0357(4) 0.1753(2) 0.6468(3) 0.0943(12) Uani 1 1 d . . . . .
N1 N 0.5701(4) 0.34430(16) 0.33954(19) 0.0415(6) Uani 1 1 d . . . . .
N2 N 0.8374(3) 0.23073(17) 0.4674(2) 0.0470(6) Uani 1 1 d . . . . .
C1 C 0.3326(4) 0.43262(19) 0.4103(2) 0.0451(7) Uani 1 1 d . . . . .
C2 C 0.1864(5) 0.4597(2) 0.4320(3) 0.0578(9) Uani 1 1 d . . . . .
H2 H 0.166871 0.444456 0.488777 0.069 Uiso 1 1 calc R U . . .
C3 C 0.0693(5) 0.5096(2) 0.3690(4) 0.0716(13) Uani 1 1 d . . . . .
H3 H -0.029498 0.526496 0.383145 0.086 Uiso 1 1 calc R U . . .
C4 C 0.0993(5) 0.5339(3) 0.2861(4) 0.0723(12) Uani 1 1 d . . . . .
H4 H 0.022375 0.568443 0.245001 0.087 Uiso 1 1 calc R U . . .
C5 C 0.2430(5) 0.5072(2) 0.2637(3) 0.0605(10) Uani 1 1 d . . . . .
H5 H 0.261805 0.522809 0.206799 0.073 Uiso 1 1 calc R U . . .
C6 C 0.3605(4) 0.4567(2) 0.3258(2) 0.0462(7) Uani 1 1 d . . . . .
C7 C 0.5185(5) 0.4286(2) 0.3015(2) 0.0509(8) Uani 1 1 d . . . . .
H7A H 0.497694 0.427939 0.233687 0.061 Uiso 1 1 calc R U . . .
H7B H 0.609867 0.467626 0.327210 0.061 Uiso 1 1 calc R U . . .
C8 C 0.4266(4) 0.23094(18) 0.4501(2) 0.0364(6) Uani 1 1 d . . . . .
C9 C 0.3906(4) 0.1688(2) 0.5071(2) 0.0428(7) Uani 1 1 d . . . . .
H9 H 0.393520 0.180844 0.568998 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3505(4) 0.0891(2) 0.4725(3) 0.0512(8) Uani 1 1 d . . . . .
H10 H 0.328365 0.047627 0.511451 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3433(5) 0.0712(2) 0.3804(3) 0.0523(8) Uani 1 1 d . . . . .
H11 H 0.315995 0.017712 0.357098 0.063 Uiso 1 1 calc R U . . .
C12 C 0.3765(5) 0.1326(2) 0.3225(2) 0.0462(8) Uani 1 1 d . . . . .
H12 H 0.370795 0.120332 0.260278 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4184(4) 0.21240(19) 0.3565(2) 0.0377(6) Uani 1 1 d . . . . .
C14 C 0.4440(4) 0.2811(2) 0.2915(2) 0.0449(7) Uani 1 1 d . . . . .
H14A H 0.481164 0.256591 0.240567 0.054 Uiso 1 1 calc R U . . .
H14B H 0.335943 0.308413 0.264171 0.054 Uiso 1 1 calc R U . . .
C15 C 0.7427(5) 0.3264(3) 0.3309(3) 0.0592(9) Uani 1 1 d . . . . .
H15A H 0.820010 0.368499 0.365440 0.071 Uiso 1 1 calc R U . . .
H15B H 0.740857 0.331152 0.265218 0.071 Uiso 1 1 calc R U . . .
C16 C 0.8117(5) 0.2418(3) 0.3661(3) 0.0611(10) Uani 1 1 d . . . . .
H16A H 0.733400 0.199503 0.332846 0.073 Uiso 1 1 calc R U . . .
H16B H 0.919204 0.233477 0.351734 0.073 Uiso 1 1 calc R U . . .
C17 C 0.8606(5) 0.1429(2) 0.4911(3) 0.0596(10) Uani 1 1 d . . . . .
H17A H 0.955544 0.121348 0.470873 0.072 Uiso 1 1 calc R U . . .
H17B H 0.759465 0.112304 0.458177 0.072 Uiso 1 1 calc R U . . .
C18 C 0.8935(6) 0.1302(3) 0.5949(3) 0.0745(13) Uani 1 1 d . . . . .
H18A H 0.794186 0.147448 0.613849 0.089 Uiso 1 1 calc R U . . .
H18B H 0.911672 0.071398 0.609112 0.089 Uiso 1 1 calc R U . . .
C19 C 1.0113(6) 0.2617(3) 0.6257(4) 0.0851(15) Uani 1 1 d . . . . .
H19A H 1.110130 0.292466 0.661198 0.102 Uiso 1 1 calc R U . . .
H19B H 0.913445 0.281390 0.644424 0.102 Uiso 1 1 calc R U . . .
C20 C 0.9845(5) 0.2772(3) 0.5232(3) 0.0663(11) Uani 1 1 d . . . . .
H20A H 0.966772 0.336187 0.510507 0.080 Uiso 1 1 calc R U . . .
H20B H 1.085126 0.260483 0.505279 0.080 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 F1 2.145(2) . ?
Bi1 N1 2.576(3) . ?
Bi1 C1 2.257(3) . ?
Bi1 C8 2.228(3) . ?
O1 C18 1.407(5) . ?
O1 C19 1.425(5) . ?
N1 C7 1.483(4) . ?
N1 C14 1.483(4) . ?
N1 C15 1.481(5) . ?
N2 C16 1.465(5) . ?
N2 C17 1.454(4) . ?
N2 C20 1.463(5) . ?
C1 C2 1.391(5) . ?
C1 C6 1.385(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(5) . ?
C6 C7 1.504(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.390(4) . ?
C8 C13 1.398(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(4) . ?
C13 C14 1.516(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.509(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.498(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.491(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 Bi1 N1 151.89(10) . . ?
F1 Bi1 C1 88.06(11) . . ?
F1 Bi1 C8 90.23(10) . . ?
C1 Bi1 N1 71.30(10) . . ?
C8 Bi1 N1 73.93(9) . . ?
C8 Bi1 C1 96.47(11) . . ?
C18 O1 C19 109.7(3) . . ?
C7 N1 Bi1 102.51(19) . . ?
C14 N1 Bi1 104.65(17) . . ?
C14 N1 C7 110.8(3) . . ?
C15 N1 Bi1 117.2(2) . . ?
C15 N1 C7 108.9(3) . . ?
C15 N1 C14 112.4(3) . . ?
C17 N2 C16 109.7(3) . . ?
C17 N2 C20 109.1(3) . . ?
C20 N2 C16 112.3(3) . . ?
C2 C1 Bi1 123.8(3) . . ?
C6 C1 Bi1 117.1(2) . . ?
C6 C1 C2 119.1(3) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 C7 119.8(3) . . ?
C5 C6 C7 120.0(3) . . ?
N1 C7 C6 111.0(3) . . ?
N1 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 Bi1 122.3(2) . . ?
C9 C8 C13 119.1(3) . . ?
C13 C8 Bi1 118.0(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C14 119.7(3) . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 C14 120.4(3) . . ?
N1 C14 C13 113.2(2) . . ?
N1 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
N1 C15 H15A 108.6 . . ?
N1 C15 H15B 108.6 . . ?
N1 C15 C16 114.8(3) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
N2 C16 C15 113.4(3) . . ?
N2 C16 H16A 108.9 . . ?
N2 C16 H16B 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 C18 110.7(3) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
O1 C18 C17 112.2(4) . . ?
O1 C18 H18A 109.2 . . ?
O1 C18 H18B 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
O1 C19 H19A 109.4 . . ?
O1 C19 H19B 109.4 . . ?
O1 C19 C20 111.0(4) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
N2 C20 C19 110.9(3) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C7 C6 -43.9(3) . . . . ?
Bi1 N1 C14 C13 -33.8(3) . . . . ?
Bi1 N1 C15 C16 65.0(4) . . . . ?
Bi1 C1 C2 C3 178.9(3) . . . . ?
Bi1 C1 C6 C5 -178.5(2) . . . . ?
Bi1 C1 C6 C7 1.2(4) . . . . ?
Bi1 C8 C9 C10 -169.3(2) . . . . ?
Bi1 C8 C13 C12 170.3(2) . . . . ?
Bi1 C8 C13 C14 -13.7(4) . . . . ?
O1 C19 C20 N2 58.4(5) . . . . ?
N1 C15 C16 N2 -64.5(5) . . . . ?
N2 C17 C18 O1 -57.2(5) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C1 C6 C7 N1 33.6(4) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C6 C7 179.5(3) . . . . ?
C2 C3 C4 C5 1.8(6) . . . . ?
C3 C4 C5 C6 -1.3(6) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C4 C5 C6 C7 -179.2(3) . . . . ?
C5 C6 C7 N1 -146.7(3) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
C7 N1 C14 C13 -143.6(3) . . . . ?
C7 N1 C15 C16 -179.4(3) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C8 C13 C14 N1 35.2(4) . . . . ?
C9 C8 C13 C12 -0.7(4) . . . . ?
C9 C8 C13 C14 175.3(3) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
C11 C12 C13 C8 -0.2(5) . . . . ?
C11 C12 C13 C14 -176.1(3) . . . . ?
C12 C13 C14 N1 -148.9(3) . . . . ?
C13 C8 C9 C10 1.3(5) . . . . ?
C14 N1 C7 C6 67.2(4) . . . . ?
C14 N1 C15 C16 -56.3(4) . . . . ?
C15 N1 C7 C6 -168.7(3) . . . . ?
C15 N1 C14 C13 94.4(3) . . . . ?
C16 N2 C17 C18 177.9(3) . . . . ?
C16 N2 C20 C19 -177.6(3) . . . . ?
C17 N2 C16 C15 165.3(3) . . . . ?
C17 N2 C20 C19 -55.8(4) . . . . ?
C18 O1 C19 C20 -58.6(6) . . . . ?
C19 O1 C18 C17 58.2(6) . . . . ?
C20 N2 C16 C15 -73.3(4) . . . . ?
C20 N2 C17 C18 54.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl02_0m
_database_code_depnum_ccdc_archive 'CCDC 2504553'
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;Department of Chemistry, University of California, San Diego
United States of America
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H46 Bi F3'
_chemical_formula_sum            'C31 H46 Bi F3'
_chemical_formula_weight         684.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.9497(8)
_cell_length_b                   17.0078(11)
_cell_length_c                   13.8407(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.688(2)
_cell_angle_gamma                90
_cell_volume                     3013.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8427
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.137
_cell_measurement_theta_min      2.338
_shelx_estimated_absorpt_T_max   0.358
_shelx_estimated_absorpt_T_min   0.280
_exptl_absorpt_coefficient_mu    5.886
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1047 before and 0.0862 after correction.
The Ratio of minimum to maximum transmission is 0.7410.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20579
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.157
_diffrn_reflns_theta_min         1.910
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5690
_reflns_number_total             6673
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.264
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.186
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6673
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C7(H7), C26(H26), C23(H23), C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C21(H21), C5(H5), C19(H19)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C25(H25A,H25B,
 H25C), C27(H27A,H27B,H27C), C8(H8A,H8B,H8C), C24(H24A,H24B,H24C), C15(H15A,
 H15B,H15C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C),
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.59497(2) 0.31793(2) 0.34458(2) 0.01249(7) Uani 1 1 d . . . . .
F2 F 0.6223(2) 0.32947(15) 0.1271(2) 0.0246(6) Uani 1 1 d . . . . .
F3 F 0.6452(2) 0.21208(15) 0.1838(2) 0.0263(6) Uani 1 1 d . . . . .
F1 F 0.7729(2) 0.29461(18) 0.2013(2) 0.0283(6) Uani 1 1 d . . . . .
C29 C 0.8631(3) 0.2742(2) 0.4276(3) 0.0146(9) Uani 1 1 d . . . . .
H29 H 0.821117 0.312288 0.382619 0.018 Uiso 1 1 calc R U . . .
C1 C 0.6820(3) 0.4187(2) 0.4306(3) 0.0130(8) Uani 1 1 d . . . . .
C7 C 0.6003(3) 0.3653(2) 0.5767(3) 0.0151(9) Uani 1 1 d . . . . .
H7 H 0.585458 0.319956 0.530696 0.018 Uiso 1 1 calc R U . . .
C2 C 0.6670(3) 0.4233(2) 0.5291(3) 0.0133(8) Uani 1 1 d . . . . .
C3 C 0.7130(3) 0.4859(2) 0.5856(3) 0.0153(9) Uani 1 1 d . . . . .
H3 H 0.704123 0.489239 0.652366 0.018 Uiso 1 1 calc R U . . .
C21 C 0.8315(3) 0.1486(2) 0.5120(3) 0.0137(8) Uani 1 1 d . . . . .
H21 H 0.905300 0.145375 0.528770 0.016 Uiso 1 1 calc R U . . .
C17 C 0.6795(3) 0.2179(2) 0.4331(3) 0.0099(8) Uani 1 1 d . . . . .
C26 C 0.8174(3) 0.0178(2) 0.5975(3) 0.0145(9) Uani 1 1 d . . . . .
H26 H 0.763312 -0.004969 0.633755 0.017 Uiso 1 1 calc R U . . .
C6 C 0.7381(3) 0.4768(2) 0.3894(3) 0.0136(8) Uani 1 1 d . . . . .
C9 C 0.4947(3) 0.4021(3) 0.5879(3) 0.0224(10) Uani 1 1 d . . . . .
H9A H 0.506122 0.448979 0.629256 0.034 Uiso 1 1 calc R U . . .
H9B H 0.452762 0.363937 0.618126 0.034 Uiso 1 1 calc R U . . .
H9C H 0.457767 0.416881 0.523360 0.034 Uiso 1 1 calc R U . . .
C31 C 0.9148(4) 0.3208(2) 0.5165(4) 0.0220(11) Uani 1 1 d . . . . .
H31A H 0.960335 0.285868 0.560341 0.033 Uiso 1 1 calc R U . . .
H31B H 0.860786 0.342638 0.551316 0.033 Uiso 1 1 calc R U . . .
H31C H 0.956333 0.363689 0.494886 0.033 Uiso 1 1 calc R U . . .
C23 C 0.4956(3) 0.1641(3) 0.4455(3) 0.0170(9) Uani 1 1 d . . . . .
H23 H 0.476462 0.220459 0.432297 0.020 Uiso 1 1 calc R U . . .
C5 C 0.7824(3) 0.5373(2) 0.4491(3) 0.0148(9) Uani 1 1 d . . . . .
H5 H 0.822068 0.576055 0.421594 0.018 Uiso 1 1 calc R U . . .
C16 C 0.6712(3) 0.2889(2) 0.2052(3) 0.0162(9) Uani 1 1 d . . . . .
C18 C 0.6152(3) 0.1598(2) 0.4667(3) 0.0114(8) Uani 1 1 d . . . . .
C10 C 0.8185(3) 0.6135(3) 0.6065(3) 0.0181(9) Uani 1 1 d . . . . .
H10 H 0.883737 0.628631 0.580671 0.022 Uiso 1 1 calc R U . . .
C30 C 0.9445(3) 0.2380(3) 0.3716(3) 0.0204(10) Uani 1 1 d . . . . .
H30A H 0.983030 0.279930 0.344094 0.031 Uiso 1 1 calc R U . . .
H30B H 0.909418 0.204875 0.318604 0.031 Uiso 1 1 calc R U . . .
H30C H 0.993289 0.205844 0.416193 0.031 Uiso 1 1 calc R U . . .
C22 C 0.7878(3) 0.2129(2) 0.4561(3) 0.0126(8) Uani 1 1 d . . . . .
C19 C 0.6622(3) 0.0965(2) 0.5203(3) 0.0132(8) Uani 1 1 d . . . . .
H19 H 0.619356 0.056783 0.541797 0.016 Uiso 1 1 calc R U . . .
C4 C 0.7715(3) 0.5438(2) 0.5468(3) 0.0134(8) Uani 1 1 d . . . . .
C25 C 0.4427(3) 0.1379(3) 0.5317(4) 0.0254(11) Uani 1 1 d . . . . .
H25A H 0.450247 0.080912 0.540202 0.038 Uiso 1 1 calc R U . . .
H25B H 0.368386 0.151589 0.518937 0.038 Uiso 1 1 calc R U . . .
H25C H 0.475647 0.164531 0.591322 0.038 Uiso 1 1 calc R U . . .
C27 C 0.8442(4) -0.0441(3) 0.5266(3) 0.0241(10) Uani 1 1 d . . . . .
H27A H 0.783158 -0.054124 0.477141 0.036 Uiso 1 1 calc R U . . .
H27B H 0.864683 -0.092862 0.562269 0.036 Uiso 1 1 calc R U . . .
H27C H 0.902249 -0.025508 0.494697 0.036 Uiso 1 1 calc R U . . .
C20 C 0.7704(3) 0.0900(2) 0.5431(3) 0.0115(8) Uani 1 1 d . . . . .
C8 C 0.6553(4) 0.3318(3) 0.6737(4) 0.0282(12) Uani 1 1 d . . . . .
H8A H 0.716612 0.301480 0.662175 0.042 Uiso 1 1 calc R U . . .
H8B H 0.607006 0.297357 0.702064 0.042 Uiso 1 1 calc R U . . .
H8C H 0.677293 0.374961 0.719015 0.042 Uiso 1 1 calc R U . . .
C24 C 0.4538(4) 0.1179(3) 0.3537(4) 0.0293(12) Uani 1 1 d . . . . .
H24A H 0.482628 0.139730 0.297937 0.044 Uiso 1 1 calc R U . . .
H24B H 0.377444 0.121633 0.341471 0.044 Uiso 1 1 calc R U . . .
H24C H 0.474525 0.062666 0.362709 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7523(4) 0.4773(2) 0.2823(3) 0.0192(9) Uani 1 1 d . . . . .
H13 H 0.714693 0.430559 0.250235 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7043(4) 0.5511(3) 0.2301(3) 0.0237(10) Uani 1 1 d . . . . .
H15A H 0.628564 0.550999 0.229954 0.036 Uiso 1 1 calc R U . . .
H15B H 0.718718 0.551604 0.162596 0.036 Uiso 1 1 calc R U . . .
H15C H 0.734799 0.598030 0.264334 0.036 Uiso 1 1 calc R U . . .
C11 C 0.8483(4) 0.5975(3) 0.7143(3) 0.0269(11) Uani 1 1 d . . . . .
H11A H 0.785160 0.587088 0.743341 0.040 Uiso 1 1 calc R U . . .
H11B H 0.884558 0.643404 0.746040 0.040 Uiso 1 1 calc R U . . .
H11C H 0.894532 0.551640 0.723597 0.040 Uiso 1 1 calc R U . . .
C12 C 0.7431(5) 0.6840(3) 0.5898(5) 0.0389(16) Uani 1 1 d . . . . .
H12A H 0.727915 0.695596 0.519757 0.058 Uiso 1 1 calc R U . . .
H12B H 0.775429 0.729993 0.624714 0.058 Uiso 1 1 calc R U . . .
H12C H 0.677974 0.671122 0.614342 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8672(4) 0.4704(3) 0.2697(4) 0.0305(12) Uani 1 1 d . . . . .
H14A H 0.904807 0.517702 0.295608 0.046 Uiso 1 1 calc R U . . .
H14B H 0.872511 0.464947 0.200080 0.046 Uiso 1 1 calc R U . . .
H14C H 0.898023 0.424137 0.305162 0.046 Uiso 1 1 calc R U . . .
C28 C 0.9139(3) 0.0373(3) 0.6728(3) 0.0238(11) Uani 1 1 d . . . . .
H28A H 0.938221 -0.010333 0.709020 0.036 Uiso 1 1 calc R U . . .
H28B H 0.895363 0.077161 0.718406 0.036 Uiso 1 1 calc R U . . .
H28C H 0.969579 0.057669 0.638985 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.284(4) . ?
Bi1 C17 2.278(4) . ?
Bi1 C16 2.349(4) . ?
F2 C16 1.356(5) . ?
F3 C16 1.370(5) . ?
F1 C16 1.330(5) . ?
C29 H29 1.0000 . ?
C29 C31 1.530(6) . ?
C29 C30 1.530(6) . ?
C29 C22 1.520(6) . ?
C1 C2 1.407(6) . ?
C1 C6 1.399(6) . ?
C7 H7 1.0000 . ?
C7 C2 1.525(6) . ?
C7 C9 1.533(6) . ?
C7 C8 1.532(6) . ?
C2 C3 1.400(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.408(6) . ?
C21 C20 1.381(6) . ?
C17 C18 1.415(6) . ?
C17 C22 1.392(6) . ?
C26 H26 1.0000 . ?
C26 C27 1.514(6) . ?
C26 C20 1.519(5) . ?
C26 C28 1.538(6) . ?
C6 C5 1.388(6) . ?
C6 C13 1.521(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C23 H23 1.0000 . ?
C23 C18 1.534(6) . ?
C23 C25 1.528(6) . ?
C23 C24 1.522(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(6) . ?
C18 C19 1.395(5) . ?
C10 H10 1.0000 . ?
C10 C4 1.519(6) . ?
C10 C11 1.508(6) . ?
C10 C12 1.541(7) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.393(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C15 1.534(6) . ?
C13 C14 1.529(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 C16 110.53(15) . . ?
C17 Bi1 C1 96.93(15) . . ?
C17 Bi1 C16 93.29(14) . . ?
C31 C29 H29 107.2 . . ?
C31 C29 C30 111.4(4) . . ?
C30 C29 H29 107.2 . . ?
C22 C29 H29 107.2 . . ?
C22 C29 C31 111.5(4) . . ?
C22 C29 C30 111.9(3) . . ?
C2 C1 Bi1 114.7(3) . . ?
C6 C1 Bi1 124.3(3) . . ?
C6 C1 C2 120.8(4) . . ?
C2 C7 H7 106.9 . . ?
C2 C7 C9 110.6(3) . . ?
C2 C7 C8 113.7(4) . . ?
C9 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C8 C7 C9 111.5(4) . . ?
C1 C2 C7 123.5(4) . . ?
C3 C2 C1 118.3(4) . . ?
C3 C2 C7 118.1(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(4) . . ?
C4 C3 H3 119.0 . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C20 C21 C22 122.0(4) . . ?
C18 C17 Bi1 116.0(3) . . ?
C22 C17 Bi1 123.7(3) . . ?
C22 C17 C18 120.3(4) . . ?
C27 C26 H26 107.6 . . ?
C27 C26 C20 110.9(3) . . ?
C27 C26 C28 110.3(4) . . ?
C20 C26 H26 107.6 . . ?
C20 C26 C28 112.6(4) . . ?
C28 C26 H26 107.6 . . ?
C1 C6 C13 123.2(4) . . ?
C5 C6 C1 118.3(4) . . ?
C5 C6 C13 118.5(4) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C18 C23 H23 107.1 . . ?
C25 C23 H23 107.1 . . ?
C25 C23 C18 113.3(4) . . ?
C24 C23 H23 107.1 . . ?
C24 C23 C18 110.9(4) . . ?
C24 C23 C25 110.9(4) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 C6 123.1(4) . . ?
C4 C5 H5 118.4 . . ?
F2 C16 Bi1 110.2(3) . . ?
F2 C16 F3 104.1(3) . . ?
F3 C16 Bi1 104.9(3) . . ?
F1 C16 Bi1 124.0(3) . . ?
F1 C16 F2 106.1(3) . . ?
F1 C16 F3 105.9(3) . . ?
C17 C18 C23 122.1(4) . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 C23 119.0(4) . . ?
C4 C10 H10 107.3 . . ?
C4 C10 C12 109.5(4) . . ?
C11 C10 H10 107.3 . . ?
C11 C10 C4 114.8(4) . . ?
C11 C10 C12 110.5(4) . . ?
C12 C10 H10 107.3 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C21 C22 C29 117.0(4) . . ?
C17 C22 C29 124.2(4) . . ?
C17 C22 C21 118.8(4) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.7(4) . . ?
C20 C19 H19 119.2 . . ?
C3 C4 C10 122.4(4) . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 C10 120.1(4) . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C21 C20 C26 122.1(4) . . ?
C21 C20 C19 118.5(4) . . ?
C19 C20 C26 119.4(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C6 C13 H13 107.8 . . ?
C6 C13 C15 111.3(4) . . ?
C6 C13 C14 112.0(4) . . ?
C15 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C14 C13 C15 110.0(4) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 C1 C2 C7 1.3(5) . . . . ?
Bi1 C1 C2 C3 -176.6(3) . . . . ?
Bi1 C1 C6 C5 176.4(3) . . . . ?
Bi1 C1 C6 C13 -3.2(6) . . . . ?
Bi1 C17 C18 C23 -0.4(5) . . . . ?
Bi1 C17 C18 C19 179.2(3) . . . . ?
Bi1 C17 C22 C29 1.6(6) . . . . ?
Bi1 C17 C22 C21 179.5(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C1 C6 C5 C4 -1.6(6) . . . . ?
C1 C6 C13 C15 118.6(4) . . . . ?
C1 C6 C13 C14 -117.8(5) . . . . ?
C7 C2 C3 C4 -177.2(4) . . . . ?
C2 C1 C6 C5 2.7(6) . . . . ?
C2 C1 C6 C13 -176.9(4) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C2 C3 C4 C10 177.8(4) . . . . ?
C17 C18 C19 C20 1.3(6) . . . . ?
C6 C1 C2 C7 175.5(4) . . . . ?
C6 C1 C2 C3 -2.3(6) . . . . ?
C6 C5 C4 C3 0.1(6) . . . . ?
C6 C5 C4 C10 -177.4(4) . . . . ?
C9 C7 C2 C1 -103.4(5) . . . . ?
C9 C7 C2 C3 74.4(5) . . . . ?
C31 C29 C22 C21 -69.0(5) . . . . ?
C31 C29 C22 C17 108.9(5) . . . . ?
C23 C18 C19 C20 -179.0(4) . . . . ?
C5 C6 C13 C15 -61.0(5) . . . . ?
C5 C6 C13 C14 62.6(5) . . . . ?
C18 C17 C22 C29 -177.0(4) . . . . ?
C18 C17 C22 C21 0.9(6) . . . . ?
C18 C19 C20 C21 0.5(6) . . . . ?
C18 C19 C20 C26 -177.1(4) . . . . ?
C30 C29 C22 C21 56.5(5) . . . . ?
C30 C29 C22 C17 -125.5(4) . . . . ?
C22 C21 C20 C26 175.8(4) . . . . ?
C22 C21 C20 C19 -1.7(6) . . . . ?
C22 C17 C18 C23 178.3(4) . . . . ?
C22 C17 C18 C19 -2.1(6) . . . . ?
C25 C23 C18 C17 -141.0(4) . . . . ?
C25 C23 C18 C19 39.4(5) . . . . ?
C27 C26 C20 C21 -83.6(5) . . . . ?
C27 C26 C20 C19 93.8(5) . . . . ?
C20 C21 C22 C29 179.1(4) . . . . ?
C20 C21 C22 C17 1.0(6) . . . . ?
C8 C7 C2 C1 130.2(4) . . . . ?
C8 C7 C2 C3 -52.0(5) . . . . ?
C24 C23 C18 C17 93.5(5) . . . . ?
C24 C23 C18 C19 -86.1(5) . . . . ?
C13 C6 C5 C4 178.0(4) . . . . ?
C11 C10 C4 C3 30.7(6) . . . . ?
C11 C10 C4 C5 -151.9(4) . . . . ?
C12 C10 C4 C3 -94.2(5) . . . . ?
C12 C10 C4 C5 83.2(5) . . . . ?
C28 C26 C20 C21 40.5(5) . . . . ?
C28 C26 C20 C19 -142.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hyvl002
_database_code_depnum_ccdc_archive 'CCDC 2504520'
loop_
_audit_author_name
_audit_author_address
'Glenn P. A. Yap'
;University of Delaware
United States of America
;
_audit_update_record             
;
2025-11-25 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_audit_creation_date             2024-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 Bi F3 N O'
_chemical_formula_sum            'C18 H19 Bi F3 N O'
_chemical_formula_weight         531.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2635(3)
_cell_length_b                   12.7354(4)
_cell_length_c                   12.9743(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.7490(10)
_cell_angle_gamma                90
_cell_volume                     1825.13(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.172
_cell_measurement_theta_min      4.002
_shelx_estimated_absorpt_T_max   0.304
_shelx_estimated_absorpt_T_min   0.200
_exptl_absorpt_coefficient_mu    19.265
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1246 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.5816.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.081
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30139
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.180
_diffrn_reflns_theta_min         4.002
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker Venture Photon III'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2999
_reflns_number_total             3209
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0166P)²+2.1657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0485
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.77171(2) 0.52836(2) 0.41167(2) 0.04171(7) Uani 1 1 d . . . . .
F1 F 0.7749(3) 0.3616(2) 0.2352(3) 0.0941(10) Uani 1 1 d . . . . .
F2 F 0.8059(3) 0.5074(2) 0.1738(2) 0.0699(7) Uani 1 1 d . . . . .
F3 F 0.9495(2) 0.4346(2) 0.3154(2) 0.0812(8) Uani 1 1 d . . . . .
O1 O 0.6928(5) 0.4883(4) 0.6096(4) 0.1065(15) Uani 1 1 d . . . . .
N1 N 0.6885(3) 0.6846(2) 0.4943(3) 0.0498(7) Uani 1 1 d . . . . .
C1 C 0.8859(3) 0.6735(3) 0.4334(3) 0.0437(8) Uani 1 1 d . . . . .
C2 C 0.9626(3) 0.6869(3) 0.3803(4) 0.0556(10) Uani 1 1 d . . . . .
H2 H 0.966001 0.635879 0.330501 0.067 Uiso 1 1 calc R U . . .
C3 C 1.0339(4) 0.7769(4) 0.4022(4) 0.0720(13) Uani 1 1 d . . . . .
H3 H 1.084980 0.786040 0.366895 0.086 Uiso 1 1 calc R U . . .
C4 C 1.0287(5) 0.8522(4) 0.4761(5) 0.0820(15) Uani 1 1 d . . . . .
H4 H 1.075978 0.912466 0.490293 0.098 Uiso 1 1 calc R U . . .
C5 C 0.9543(4) 0.8386(4) 0.5286(5) 0.0736(13) Uani 1 1 d . . . . .
H5 H 0.951962 0.889688 0.578816 0.088 Uiso 1 1 calc R U . . .
C6 C 0.8825(4) 0.7506(3) 0.5084(3) 0.0539(10) Uani 1 1 d . . . . .
C7 C 0.8022(4) 0.7371(4) 0.5690(4) 0.0625(11) Uani 1 1 d . . . . .
H7A H 0.844292 0.695744 0.637839 0.075 Uiso 1 1 calc R U . . .
H7B H 0.784549 0.805359 0.591346 0.075 Uiso 1 1 calc R U . . .
C8 C 0.5982(3) 0.5896(3) 0.2701(3) 0.0473(9) Uani 1 1 d . . . . .
C9 C 0.5359(4) 0.5329(4) 0.1707(4) 0.0646(12) Uani 1 1 d . . . . .
H9 H 0.567481 0.469916 0.159297 0.078 Uiso 1 1 calc R U . . .
C10 C 0.4267(4) 0.5696(6) 0.0885(4) 0.0861(17) Uani 1 1 d . . . . .
H10 H 0.384642 0.530635 0.022228 0.103 Uiso 1 1 calc R U . . .
C11 C 0.3801(4) 0.6620(6) 0.1034(5) 0.0897(19) Uani 1 1 d . . . . .
H11 H 0.307497 0.686930 0.046833 0.108 Uiso 1 1 calc R U . . .
C12 C 0.4408(4) 0.7190(4) 0.2029(4) 0.0722(14) Uani 1 1 d . . . . .
H12 H 0.408252 0.781819 0.213348 0.087 Uiso 1 1 calc R U . . .
C13 C 0.5501(3) 0.6830(3) 0.2874(3) 0.0529(10) Uani 1 1 d . . . . .
C14 C 0.6174(4) 0.7491(3) 0.3927(4) 0.0599(11) Uani 1 1 d . . . . .
H14A H 0.671258 0.796668 0.378741 0.072 Uiso 1 1 calc R U . . .
H14B H 0.559719 0.791076 0.407534 0.072 Uiso 1 1 calc R U . . .
C15 C 0.6123(4) 0.6571(4) 0.5526(4) 0.0717(13) Uani 1 1 d . . . . .
H15A H 0.537188 0.627069 0.496654 0.086 Uiso 1 1 calc R U . . .
H15B H 0.592248 0.721148 0.581050 0.086 Uiso 1 1 calc R U . . .
C16 C 0.6687(6) 0.5814(5) 0.6505(5) 0.0871(16) Uani 1 1 d . . . . .
H16A H 0.743145 0.610603 0.708399 0.105 Uiso 1 1 calc R U . . .
H16B H 0.613864 0.568614 0.684986 0.105 Uiso 1 1 calc R U . . .
C17 C 0.7644(9) 0.4200(8) 0.6982(8) 0.173(5) Uani 1 1 d . . . . .
H17A H 0.768750 0.352857 0.666648 0.259 Uiso 1 1 calc R U . . .
H17B H 0.729022 0.411950 0.750788 0.259 Uiso 1 1 calc R U . . .
H17C H 0.844435 0.448655 0.737792 0.259 Uiso 1 1 calc R U . . .
C18 C 0.8295(4) 0.4555(3) 0.2721(4) 0.0531(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N1 2.665(3) . ?
Bi1 C1 2.262(4) . ?
Bi1 C8 2.261(4) . ?
Bi1 C18 2.399(4) . ?
F1 C18 1.353(5) . ?
F2 C18 1.351(5) . ?
F3 C18 1.355(5) . ?
O1 C16 1.381(7) . ?
O1 C17 1.405(8) . ?
N1 C7 1.469(5) . ?
N1 C14 1.474(5) . ?
N1 C15 1.476(5) . ?
C1 C2 1.396(5) . ?
C1 C6 1.395(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(6) . ?
C6 C7 1.514(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.383(6) . ?
C8 C13 1.389(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.359(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(6) . ?
C13 C14 1.508(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.503(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 N1 70.37(12) . . ?
C1 Bi1 C18 92.31(14) . . ?
C8 Bi1 N1 71.29(12) . . ?
C8 Bi1 C1 97.61(13) . . ?
C8 Bi1 C18 90.14(14) . . ?
C18 Bi1 N1 151.95(12) . . ?
C16 O1 C17 112.2(7) . . ?
C7 N1 Bi1 100.7(2) . . ?
C7 N1 C14 111.1(3) . . ?
C7 N1 C15 113.6(3) . . ?
C14 N1 Bi1 103.7(2) . . ?
C14 N1 C15 109.3(3) . . ?
C15 N1 Bi1 117.8(3) . . ?
C2 C1 Bi1 123.4(3) . . ?
C6 C1 Bi1 117.2(3) . . ?
C6 C1 C2 119.3(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(5) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 120.4(4) . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 C7 119.9(4) . . ?
N1 C7 C6 110.7(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 Bi1 121.4(3) . . ?
C9 C8 C13 119.8(4) . . ?
C13 C8 Bi1 118.7(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(5) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(5) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 119.1(4) . . ?
C8 C13 C14 121.4(3) . . ?
C12 C13 C14 119.4(4) . . ?
N1 C14 C13 112.2(3) . . ?
N1 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N1 C15 H15A 108.5 . . ?
N1 C15 H15B 108.5 . . ?
N1 C15 C16 115.1(4) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
O1 C16 C15 108.8(4) . . ?
O1 C16 H16A 109.9 . . ?
O1 C16 H16B 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F1 C18 Bi1 110.2(3) . . ?
F1 C18 F3 104.8(3) . . ?
F2 C18 Bi1 120.7(3) . . ?
F2 C18 F1 103.2(3) . . ?
F2 C18 F3 103.6(3) . . ?
F3 C18 Bi1 112.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Bi1 N1 C7 C6 45.9(4) . . . . ?
Bi1 N1 C14 C13 37.3(4) . . . . ?
Bi1 N1 C15 C16 55.5(5) . . . . ?
Bi1 C1 C2 C3 -177.2(3) . . . . ?
Bi1 C1 C6 C5 177.3(3) . . . . ?
Bi1 C1 C6 C7 -1.7(5) . . . . ?
Bi1 C8 C9 C10 176.4(4) . . . . ?
Bi1 C8 C13 C12 -177.3(3) . . . . ?
Bi1 C8 C13 C14 6.3(5) . . . . ?
N1 C15 C16 O1 -60.8(6) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C1 C6 C7 N1 -36.1(5) . . . . ?
C2 C1 C6 C5 0.2(6) . . . . ?
C2 C1 C6 C7 -178.7(4) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
C3 C4 C5 C6 -0.5(9) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C4 C5 C6 C7 179.2(5) . . . . ?
C5 C6 C7 N1 145.0(4) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C7 N1 C14 C13 144.6(3) . . . . ?
C7 N1 C15 C16 -61.8(5) . . . . ?
C8 C9 C10 C11 0.8(8) . . . . ?
C8 C13 C14 N1 -33.8(5) . . . . ?
C9 C8 C13 C12 -1.4(6) . . . . ?
C9 C8 C13 C14 -177.8(4) . . . . ?
C9 C10 C11 C12 -1.5(9) . . . . ?
C10 C11 C12 C13 0.8(8) . . . . ?
C11 C12 C13 C8 0.7(7) . . . . ?
C11 C12 C13 C14 177.2(4) . . . . ?
C12 C13 C14 N1 149.7(4) . . . . ?
C13 C8 C9 C10 0.7(7) . . . . ?
C14 N1 C7 C6 -63.5(4) . . . . ?
C14 N1 C15 C16 173.5(4) . . . . ?
C15 N1 C7 C6 172.8(4) . . . . ?
C15 N1 C14 C13 -89.2(4) . . . . ?
C17 O1 C16 C15 169.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
